EXP-PR-RT030-EN-R0 - 1 - Intro HC PDF

THEORY OUTLINE
INTRODUCTION TO HYDROCARBONS
TRAINING MANUAL
Course EXP-PR-RT030
Revision 0.1
Exploration & Production
Theory Outline
Introduction to Hydrocarbons
THEORY OUTLINE
INTRODUCTION TO HYDROCARBONS
CONTENTS
1. OBJECTIVES ..................................................................................................................4
2. INTRODUCTION TO THE ORGANIC CHEMISTRY OF HYDROCARBONS ..................5
2.1. BASICS .....................................................................................................................5
2.2. ORIGIN OF HYDROCARBONS ................................................................................8
2.3. CARBON AND HYDROGEN.....................................................................................9
2.4. ISOMERS................................................................................................................11
2.4.1. Definition...........................................................................................................11
2.4.2. Constitutional isomers ......................................................................................12
2.4.3. Stereoisometry..................................................................................................12
2.4.4. Alkyl radicals.....................................................................................................13
3. THE SIX DIFFERENT HYDROCARBON GROUPS ......................................................15
3.1. THE ALKANE GROUP............................................................................................15
3.1.1. Linear or normal alkanes (n) .............................................................................15
3.1.2. Carbon chain alkanes or isomers (i) .................................................................17
3.2. THE ALKENE GROUP............................................................................................18
3.3. THE ALKYNE GROUP............................................................................................20
3.4. THE CYCLANE GROUP .........................................................................................21
3.5. THE AROMATIC GROUP .......................................................................................22
3.6. THE CYCLEN GROUP ...........................................................................................22
4. MAIN PHYSICAL CHARACTERISTICS OF HYDROCARBONS...................................23
4.1. GENERAL ASPECTS .............................................................................................23
4.2. STATE CHANGING TEMPERATURES ..................................................................25
4.3. DENSITY / API ......................................................................................................25
4.4. VISCOSITY .............................................................................................................25
4.5. COMBUSTION HEAT .............................................................................................25
5. INTRODUCTION TO HYDROCARBON PROCESSING ...............................................26
5.1. CRUDE OIL PROCESSING ....................................................................................26
5.2. GAS PROCESSING................................................................................................28
5.2.1. Transport in gaseous form ................................................................................29
5.2.2. Transport in liquid form .....................................................................................29
5.2.2.1. Liquefied natural gas: LNG.........................................................................31
5.2.2.2. LPG liquefied petroleum gas ...................................................................32
5.2.2.3. NGL - Natural Gas Liquids .........................................................................32
5.2.2.4. Condensates or natural gasoline................................................................33
6. HYDROCARBONS AS A SOURCE OF ENERGY.........................................................34
6.1. INTRODUCTION.....................................................................................................34
6.2. COMBUSTION OF ALKANES ................................................................................34
6.2.1. Example: the combustion of methane:..............................................................34
7. NAMES ASSOCIATED WITH HYDROCARBONS ........................................................36
7.1. GAS AND CRUDE ..................................................................................................36
Training course: EXP-PR-RT030-EN
Last revised: 26/04/2007 Page 2 / 48
Theory Outline
7.2. NATURAL GAS .......................................................................................................36

7.3. CRUDE OIL.............................................................................................................36
7.4. DENSITY OF OIL: THE API DEGREE ....................................................................37
7.5. ASSOCIATED GAS.................................................................................................37
7.6. ARABIAN LIGHT .....................................................................................................37
7.7. BRENT ....................................................................................................................38
7.8. LIGHT AND HEAVY OILS (HYDROCARBONS) .....................................................38
7.9. TOE: TONNE OIL EQUIVALENT ............................................................................38
7.10. GOR (Gas Oil Ratio) .............................................................................................38
7.11. BSW (Bottom Sediment and Water also known as watercut).............................38
7.12. HYDRATES...........................................................................................................39
7.13. DEW POINT ..........................................................................................................39
7.14. WATER CONTENT ...............................................................................................39
7.15. WOBBE INDEX .....................................................................................................40
8. EXERCISES ..................................................................................................................41
9. GLOSSARY ...................................................................................................................44
10. LIST OF FIGURES ......................................................................................................45
11. LIST OF TABLES ........................................................................................................46
12. EXERCISE SOLUTIONS .............................................................................................47

Theory Outline
1. OBJECTIVES
The objective of this course is to allow future operators to understand the bases of the
hydrocarbons domain. Upon conclusion of this course, they should be able to:
Explain the origin of hydrocarbons
Interpret the basic chemical principles of Carbon - Hydrogen bonds
Distinguish hydrocarbon components by their names and formulas
Define the composition of isomers
Name the different hydrocarbon groups
Write the chemical formulas of the components in the groups above
Define the main physical characteristics of hydrocarbons
Interpret changes of state in hydrocarbons
Integrate Pressure and Temperature values to define the characteristics of

hydrocarbons
Explain, interpret density terms, API, viscosity, combustion heat, and any other term
relative to hydrocarbon production
Name the different stages in the processing of crude oil
Name the different states in the processing of a natural gas
Differentiate the different solutions for transporting hydrocarbons in gas and / or liquid
form
Interpret the combustion of a liquid and / or gas hydrocarbon
Distinguish the different names of crude oils and gases
Define, compare and calculate with the different measurement units associated with
hydrocarbons
Interpret the terms and characteristics such as GOR, dew point, BSW (or watercut),
water content, Wobbe index and any other term employed in the routine activities of
an operator.

Theory Outline
2. INTRODUCTION TO THE ORGANIC CHEMISTRY OF

HYDROCARBONS
2.1. BASICS
Organic chemistry is the study of molecules which contain carbon and hydrogen atoms.
This is the common point between all organic molecules. Some molecules contain only
carbon and hydrogen atoms whilst others also contain other atoms (for example, oxygen,
nitrogen atoms, etc.).
Figure 1: Propane Figure 2: Glycol Figure 3: Ethylamine
A wide range of organic molecules therefore exist and the thing that differentiates them is
the number and different types of atoms which they contain.
Another characteristic which may differentiate these molecules is their structure (a single
bond or a double bond between two atoms for example), and the way in which these
arrangements are made in space (flat or other molecule).
From a physical point of view, each given molecule is associated with precise
characteristics. Certain molecules with similar physical/chemical behaviour are grouped
together in families which makes it possible to examine the characteristics of a given
family as an initial approach.
For the purposes of this course, we will be concentrating on the study of hydrocarbon
molecules which are made up only of carbon and hydrogen. This family is divided into 6
groups but the 5 most important ones are:
Alkanes or paraffins,
Alkenes or olefins (former name),
Alkynes or acetylenes,
cyclanes or cyclo-alkanes ou les naphtenes
aromatics.
Theory Outline
Name of the function/ group Structure of the group Comments
Consisting only of atoms

connected by single
Alkane
bonds
Contains at least one

Alkene
double bond
Presence of a triple bond

Alkyne
between two carbons
cyclopropane cyvlobutane cyclohexane, etc

Presence of 2 hydrogen
Cyclo-alkane atoms per carbon atom,
with a ring structure
Presence of a 6-atom
cycle with alternating
Aromatics
single and double bonds
(benzene core)
Table 1: The most important hydrocarbons

Theory Outline
A basic specificity of this group is the fact that the hydrocarbon molecules of each group
have different boiling point temperatures.
It is this characteristic which makes it possible to manufacture finished (marketable)

products using treatment processes which allow for the selective separation of the different
types of hydrocarbon molecules (e.g. distillation, etc.).

Theory Outline
2.2. ORIGIN OF HYDROCARBONS
Fossil hydrocarbons are the components of petroleum and natural gas and are produced
by the decomposition of organic matter accumulated more than 500 million years ago.
These compounds (organic molecules) are formed exclusively of carbon and hydrogen.
However, the hydrocarbons are mixed with other, often undesirable, elements (nitrogen,
oxygen, sulphur, etc.).
Petroleum is always composed mainly of hydrocarbons, of which alkanes are the main
compounds (which can reach more than forty carbon atoms). It also contains cyclanes,
aromatics, and products containing sulphur, nitrogen and oxygen in variable quantities
depending on the deposit.
It is therefore necessary to separate these different products (distillation), transform them

chemically (cracking and reforming) and purify them (actual refining) to obtain usable
products.
All these operations are carried out in refineries and the procedure is known as refining.

Theory Outline
2.3. CARBON AND HYDROGEN
Carbon and hydrogen are the 2 components of hydrocarbons.
The molecules consisting of C and H atoms represent 90% (in weight) of the natural
hydrocarbons and the remainder consists mainly of nitrogen, oxygen and sulphur.
If we refer to what has been said about the composition of the molecules:
Carbon possesses 6 electrons (see periodic table) and the layer k is saturated
with 2 electrons and it possesses 4 electrons on layer L, there are therefore 4
available spaces remaining for electrons of other atoms and it is said that
carbon has a valency of 4.
Hydrogen possesses 1 electron (see periodic table), therefore only layer K is

occupied by an electron and there is 1 available space for one electron from
another atom.
Therefore, a wide range of structures is possible (and therefore molecule types) containing
only C and H atoms, not only depending on the number of atoms involved but also
depending on the type of bond between these atoms.
For example, molecules with the maximum amount of hydrogen atoms are said to be
saturated and are Alkanes.
These organic molecules can be represented in a variety of ways, the 3 main ones being:
representation by an empirical formula: CH4 (methane), C2H6 (ethane)
semi-developed formula CH4 and CH3-CH3
developed representation.
Figure 4: Methane CH4 Figure 5: Ethane C2H6
Whilst it is not possible to use a single formula to define hydrocarbons, we can

nevertheless use the different possible bonds between the carbon and hydrogen to group

Theory Outline
hydrocarbons together in six different families whose components possess similar

properties.
Alkanes (saturated aliphatic carbonaceous chains)
Alkenes (unsaturated aliphatic carbonaceous chains)
Alkynes (unsaturated carbonaceous chains comprising a triple carbon/carbon

bond)
Cyclanes (saturated alicyclic carbonaceous chains )
Aromatics (unsaturated cyclic carbonaceous chains comprising a hexagonal

carbon cycle)
Cyclens (unsaturated cyclic carbonaceous chains )
Comments:
A molecule is said to be saturated when each carbon atom which composes it

contains the maximum possible number of hydrogen atoms (all the carbon bonds
are single). It is said to be saturated because hydrogen cannot be added to this
molecule.
A molecule (saturated or otherwise) is said to be aliphatic when its carbon chain is

open and it does not possess a closed carbon cycle (these are alkanes, alkenes
and alkynes)
A molecule is said to be cyclic when its carbon chain closes on itself without there
being any aromatic cycle (these are cyclanes and cyclens).
A molecule is said to be aromatic when it possesses an unsaturated cycle of 6

carbon atoms.
Although we shall be examining the main hydrocarbons, the emphasis will be placed on
paraffinic hydrocarbons and alkanes since alkanes are found throughout the entire oil
exploitation chain.

Theory Outline
2.4. ISOMERS
We have seen that it is useful to group hydrocarbons together in families in order to

obtain molecules with similar properties with these groups corresponding to molecules of a
similar constitution (example:
Alkanes are saturated aliphatic carbonaceous chains).
Conversely, identical molecules also exist (by their empirical formula) which have different
properties. These molecules are known as isomers.
2.4.1. Definition
There is only one methane, one ethane and one propane, but using butane there are
several possibilities for bonding carbon and hydrogen atoms.
The isomer is a molecule with the same empirical formula as the normal molecule, the
difference being that the carbon atoms of the normal molecule form a chain whereas the
isomer possesses a different semi-developed formula (therefore a different atom
arrangement and structure) and different properties or a different atom arrangement in
space.
Isomers are molecules with the same empirical formula but different structures.
The name is often preceded by the letters n or i to differentiate between the normal
molecule and the corresponding isomer,
Thus there are two alkanes with four carbon atoms: normal butane and isobutane.
They have the same formula C4H10, but are differentiated notably by their boiling point
temperature.
The number of isomers increases rapidly in excess of six carbon atoms.
There are 2 types of isomer:
Constitutional isomers for which there is only on spatial geometry possible for the
molecule concerned are known as isomers.
Isomers which can be differentiated by their spatial geometry are known as

stereoisomers

Theory Outline
No of C. atoms No of isomers No of C. atoms No of isomers

4 2 9 35
5 3 10 75
6 5 12 355
7 9 15 4347
8 18 20 366319
Table 2: Number of alkane isomers
2.4.2. Constitutional isomers
A molecule which possesses n carbon atoms and 2n+2 hydrogen atoms if n > 3, may
present branching (non-linear carbon backbone).
This is the case of butane and 2-methylpropane which have the same empirical formula
C4H10
In order to determine the name of a branched alkane, we consider that it consists of a

principal chain to which more or less complex groups are attached. The main groups are
known as alkyls:
The name given to the molecule is the name of the longest linear chain in which alkyl
groups are added (see below) to numbered carbons.
2.4.3. Stereoisometry
When we consider a molecule to be fully developed in space, new cases of isometry in

addition to constitutional isometry may exist. They are known as spatial isometries or
stereoisometries (the molecules have the same formula as the normal molecule or the
constitutional isomer but do not have the same properties).
Two stereoisomers have the same semi-developed formula but different forms in three-
dimensional space.
We will consider only stereoisometry with the configuration Z / E (the prefixes come from
German Z: zusammen = together, E: entgegen: opposing)
Comments:
Z and E isomerism can be applied to all molecules of the type CHA = CHB. Groups A and
B are not hydrogen atoms.

Theory Outline
The 2 groups A and B are diametrically

The 2 groups A and B are together
opposed
Figure 6: Stereoisomers
NB: isomers have relatively little importance for the oil industry
2.4.4. Alkyl radicals
Alkyl radicals are derivatives of an alkane which lacks hydrogen and which can therefore
be bonded to a carbon chain by forming a branch known as an alkyl radical.
The name linear alkyl radicals derives from the linear alkane by replacing the ending ane
by yl; the first 5 Alkyl radicals are:
Empirical
Radical Semi-developed formula
formula
Methyl CH3 - CH3 -

Ethyl C2H5 - CH3 - CH2-
Propyl C3H7 - CH3 - CH2 - CH2 -
Isopropyl C3H7 - CH3 - CH (CH3) -
Butyl C4H9 - CH3 - CH2 - CH2 - CH2 -
Table 3: The first 5 alkyl radicals

Theory Outline
Explanations concerning the definition method for Alkyl radical isomers:
The longest carbon chain is identified. This is the one which gives the alkane its
name.
The name (without the final e) of the group attached to the principal chain is added
as a prefix. Its position is identified by numbering the principal chain to give the
smallest number to the carbon carrying the group. This name is placed in front of
the group name.
In the case of several identical groups, the prefix di-, tri-, ttra- is placed in front of
the group name.
In the case of different groups, they are named in alphabetical order. The smallest
number is allocated to the group in first position in alphabetical order.
3-ethyl-5-methylhexane 2,4-dimethyl hexane
3-ethyl-5-methyl-4-propylheptane
Figure 7: Iso-alkanes

Theory Outline
3. THE SIX DIFFERENT HYDROCARBON GROUPS
3.1. THE ALKANE GROUP
The alkanes: CnH2n+2 (or saturated aliphatic hydrocarbons):
These are molecules whose carbon atom chain consists only of single bonds (each carbon
atom possesses 4 bonds either with H atoms or with a C atom to form a chain).
All the possible carbon bonds are used, which is why these molecules are known as
saturated aliphatic hydrocarbons.
General alkane formula: CnH2n+2 irrespective of whether their carbon backbone is linear or
branched.
A distinction is made between normal molecules (n) with a linear chain structure and
isomolecules (i) with a branched structure (iso as in isomer)
As from five carbon atoms, alkanes are liquids or solids in their natural state (it is
commonly said that the liquids are C5+).
3.1.1. Linear or normal alkanes (n)
These are alkanes with a linear carbon backbone (with no branching).
The beginning of the name of a linear alkane depends on the number of carbon atoms in
the molecule and the names ends in "ane"
Number of C 1 2 3 4 5 6 7 8 9 10
prefix meth eth prop but pent hex hept oct non dec
Table 4: The linear alkanes
This accounts for the names: methane, ethane, propane, butane,pentane...with the
respective empirical formulae C1H4, C2H6, C3H8, C4H10, C5H12,

Theory Outline
A few representations:
Figure 8: Methane CH4 Figure 9: Ethane C2H6 Figure 10: Propane C3H8
(gas) (gas) (gas)
Figure 11: Butane C4H10 (gas) Figure 12: Pentane C5H12 (liquid)
Melting point Boiling point

Name Molecule State at 25oC
(oC) (oC)
methane CH4 -182 -162 gas

ethane C2H6 -183 -88.7 gas
propane C3H8 -188 -42. gas
butane C4H10 -138 -0.5 gas
pentane C5H12 -130 36 liquid
hexane C6H14 -95 68.9 liquid
heptane C7H16 -90.6 98.4 liquid
octane C8H18 -56.8 125.6 liquid
nonane C9H20 -51 150.8 liquid
decane C10H22 -29.7 174.1 liquid
undecane C11H24 -24.6 195.9 liquid
dodecane C12H26 -9.6 216.3 liquid
eicosane C20H42 36.8 343 solid
triacontane C30H62 65.8 449.7 solid
Table 5: Linear saturated hydrocarbons or Alkanes

Theory Outline
The table above shows that the compounds C1 to C4 (methane to butane) are gaseous at
room temperature, in excess of five carbon atoms the compounds are liquid and in excess
of fifteen carbon atoms they are solids.
3.1.2. Carbon chain alkanes or isomers (i)
By applying what has been outlined in the section on Alkyl radicals, it is possible to
describe the isomers of the first 3 Alkanes
Isomers of butane C4H10
Butane, whose empirical formula is C4H10, has two common isomers, normal butane (n-
butane) and 2-methyl-propane (formerly isobutane), whose empirical formulae are as
follows:
CH3-CH2-CH2-CH3 CH3-CH(CH3)-CH3
Figure 13: n-butane C4H10 Figure 14: 2-methyl-propane(isobutane)

C4H10
A methyl group (CH3-) has attached itself to the second carbon of a propane to form the
methyl-propane isomer, which explains the origin of the name 2-methylpropane.
Pentane isomers C5H12:
Using the same principle as for butane isomers, 3 isomers exist for pentane
CH3-CH2-CH2-CH2-CH3 n-pentane C5H12
CH3-CH(CH3)-CH2-CH3 2-methylbutane C5H12
CH3-C(CH3)2-CH3 2,2-dimethylpropane C5H12

Theory Outline
Hexane isomers C6H14:
Still using the same principle, the 5 hexane isomers are:
CH3- CH2-CH2-CH2-CH2-CH3 n-hexane C6H14
CH3-CH(CH3)-CH2-CH2-CH3 2-methylpentane C6H14
CH3- CH2-CH(CH3)-CH2-CH3 3-methylpentane C6H14
CH3-C(CH3)2-CH2-CH3 2,2-dimethylbutane C6H14
CH3-C(CH3)-CH(CH3)-CH3 2,3-dimethylbutane C6H14
3.2. THE ALKENE GROUP
The Cn H2n alkenes (or unsaturated hydrocarbons with only one double bond):
Alkenes are unsaturated hydrocarbons which possess only one double bond. Their
general formula is therefore derived from the alkane formula after removing 2 H atoms.
Alkenes are also known as oleofines, literally to make oil because they have a tendency
to remain in the liquid state when they cool.
The name of an alkene is derived from the name of the corresponding alkane by replacing
the ending ane with the ending ene.
Figure 15: Alkane: Ethane C2H6 Figure 16: Alkene: Ethene C2H4
The double bond may be located at different points in the chain. To specify this position we
indicate (in the name) the position of the double bond by numbering the carbon atoms in
the carbon chain giving the carbon atoms with a double bond the smallest numbers (this
numbering is not applicable for the first two alkenes, namely ethane, commonly known as
ethylene, and propene).
Only then do we consider the numbers of the carbon atoms in which the methyl, ethyl
groups etc. are found.

Theory Outline
Ethene (ethylene) Propene But-1-ene
But-2-ene (2 stereoisomers) Pent-1-ene
Methylpropene 3-ethyl-2-methylpent-2-ene
2,3-diethylhex-1-ene
Figure 17: Alkenes
Certain alkenes possess several doubles bonds. Alkenes with 2 double bonds are known
as dienes and those with 3 are known as trienes.

Theory Outline
3.3. THE ALKYNE GROUP
The Alkynes: Cn H2n-2 (or unsaturated hydrocarbons with a single triple bond):
An alkyne is a hydrocarbon whose molecule contains a triple carbon-carbon bond.
Alkynes are therefore unsaturated hydrocarbons as a given carbon atom is not surrounded
by 4 distinct elements due to the triple bond between the carbons.
Particular reference should be made to the structure of the ethyne molecule, commonly
known as acetylene (deceptive ending as it is similar to the alkene family):
Compound External electrons Lewis model
C: 4 external electrons
H: 1 external electron
Ethyne (acetylene) (4)2 + (1)2 = 10 electrons
5 bonding doubles
Figure 18: The alkynes

Theory Outline
3.4. THE CYCLANE GROUP
The Cyclanes: CnH2n (or saturated alicyclic hydrocarbons):
Examples:
C6H12 C9H18
cyclohexane 1-ethyl-3-methylcycohexane
Figure 19: Cyclanes

Theory Outline
3.5. THE AROMATIC GROUP
(or unsaturated hydrocarbons with a benzenic cycle):
The aromatics are unsaturated hydrocarbons which possess one or more phenyl radicals
(see representation below) bonded to carbon chains.
There are at least 6 carbons.
Empirical formula: C6H5-Y: C6H5 is the phenyl radical and Y a molecule attached to this
radical..
Figure 20:Phenyl Radical C6H5 Figure 21:Benzene C6H6
Benzene C6H6 is the simplest aromatic hydrocarbon
3.6. THE CYCLEN GROUP
(or unsaturated alicyclic hydrocarbons):
Cyclens are unsaturated alicyclic hydrocarbons which possess one or more double bonds
(C=C).

Theory Outline
4. MAIN PHYSICAL CHARACTERISTICS OF HYDROCARBONS
4.1. GENERAL ASPECTS
In general terms we have seen that the characteristics of a hydrocarbon are directly linked
to the family (group) to which it belongs.
Crude oil and natural gas contain different components. Depending on the characteristics
of the alkanes we have seen that the compounds C1 to C4 are gaseous in their natural
state whilst from pentane onwards, hydrocarbons are liquid.
In fact, an oil or a gas in its natural state will have more or less the same components; it is
the proportion of these components in the mixture which determines whether the it is a
liquid or a gas, as shown in the table below.
Figure 22: Composition of a crude oil and raw natural gas
Within the alkane family, these characteristics are directly linked to the number of carbon
atoms making up the molecule as shown in the table below.

Theory Outline
Name Methane Ethane Propane Butane
Empirical formula CH4 C2H6 C3H8 C4H10
Molar mass (g.mol-1) 16 30 44 58
Density in Kg/l (liquid) 0.3 0.37 0.51 0.58
Densityof gas at15c and 760mmHg in Kg/m3 0.667 1.27 1.86 2.45
Melting temperature (C) -182 -183 -188 -138
Boiling point temperature (C) - P = 101325

-162 -88,7 -42 -0,5
Pa
Vapour pressure10C (Kg/cm2) 370 32 6.2 1.5
Litres of gas obtained from a litre of liquid 443 294 273 238
Net calorific value (kcal/m3 of gas) 9490 16630 23660 30665
Gross calorific value (Kcal/Kg) 13288 12417 11980 11586
Energy released by the combustion of one

890 1 560 2 220 2 880
mole (kJ.mol-1)
Energy released by the combustion of one

55 600 52 000 50 400 49 700
kilogramme (kJ.kg-1)
Table 6: Properties of alkanes

Theory Outline
We have therefore seen that production of crude oil is always associated with the
production of gas (associated gas). This gas is obtained by degassing the crude at
different separation levels (the recovery of light hydrocarbons C1 to C4)
In addition, the production of gas from a gas field is generally associated with the
production of a certain quantity of liquid hydrocarbons (from pentane, known as
condensates) which require a specific installation before they can be commercialised.
4.2. STATE CHANGING TEMPERATURES
The length of the carbon chain affects the melting and boiling point temperatures. These
state changing temperatures increase with the length of the carbon chain.
We have seen that at a normal temperature with five carbon atoms, alkanes with 5 to 16 C
atoms are liquid and these are the ones which are stored.
4.3. DENSITY / API
The density compared with air for gaseous alkanes or compared with water for liquid or
solid alkanes also increases with the length of the carbon chain (see details on the API
degree in the final chapter).
API degree (temp)= (141.5/ Density at temp) 131.5.
Density ( temp) = 141.5/( 131.5 + API at temp)
4.4. VISCOSITY
The viscosity of alkanes varies rapidly depending on the number of carbon atoms which
they contain; when the number of carbon atoms in an alkane is greater than 16 it solidifies
at a temperature exceeding 18C.
4.5. COMBUSTION HEAT
The combustion heat of alkanes with N carbon atoms is approximately 658 N+ 243
kJ/mole. Since the first ones are relatively richer in hydrogen, their combustion heat is
slightly higher.
It has also been shown that the calorific value, or the quantity of heat emitted by the
combustion of 1 kg of alkane, tends towards a limit of 46 000 kJ/kg when N increases
indefinitely.

Theory Outline
5. INTRODUCTION TO HYDROCARBON PROCESSING
5.1. CRUDE OIL PROCESSING
Crude oil is a mixture of a wide range of hydrocarbon molecules in which alkanes, notably
linear ones, are predominant. The proportions of the mixture vary from one reservoir to the
next and may vary over time for a given reservoir.
Commercial products must correspond to specific characteristics. It is therefore necessary

to obtain precise specific products from a crude oil, which involves transforming the crude
into a series of products with specific hydrocarbon groups: this is achieved by distillation.
The lightest oils are the most highly sought after by refiners as they directly give large
quantities of light cuts with a high value (see introduction to the treatment of crude oil).
Conversely, heavy oils give lager quantities of products such as asphalts and residual fuel
which either have to be sold as they are at a low price or converted into lighter cuts,
notably by hydrocracking (addition of hydrogen).
Figure 23: The distillation cuts

Theory Outline
The principle of distillation (or fractionating) is simply based on the fact that the boiling
point temperatures of different alkanes are clearly separated between one alkane group
and the next, which is known as fractionating by cut.
The fact that not all hydrocarbons pass through the gaseous state at the same
temperature is related to the molar mass of the molecule concerned. The greater the
volatility of a hydrocarbon, the smaller its molar mass (small number of carbon atoms).
In an industrial context, this distillation is conducted in a 40 to 60 meter high tower

comprising up to 50 plates. The crude is heated in the furnace to 370C and transmitted to
the tower where the pressure is equal to atmospheric pressure (atmospheric distillation).
The products collected on the different levels (the least volatile at the bottom and the most
volatile at the top) are mixtures with similar properties and are known as cuts:
The different distillation cuts obtained along the column are:
At the top of the column, the most volatile products are collected in their gaseous
state (C1-C4).
The boiling point temperature of the mixture decreases with its height in the
column and gas oils (C13-C20), kerosene (C10-C13), jet fuel and naphtha (C5-C10)
are separated allowing for the production of normal and super petrol.
At the bottom of the column are the heaviest hydrocarbons (C>20, with more than
20 carbon atoms per molecule), known as atmospheric residue. These are the
ones with the highest boiling point. In order to undergo a more complex separation
they must be distilled in a vacuum.
The most precise cuts can often be obtained with different temperature ranges which
correspond to specific recovery heights in the distillation column.
Cuts C1-C4: the combinations of alkanes with molecules of CH4 to C4H10)..

(these are the lightest), are gaseous at normal pressure and temperature and are
most commonly used as combustible gases (domestic and industrial use) and as
raw materials in the petrochemical industry.
Cuts C5-C6: boiling point 20-60C

Give solvents and petroleum ether
Cuts C6-C7: (boiling point 60-100C)

Give light naphtha or white spirit and are mainly used as solvents.
Cut C6-C11 (boiling point 60-200C)

Gives gasoline, the basis for the manufacturing of fuels, and also, for the naphtha
part (C6-C10), the raw material which is subjected to steam cracking for the
petrochemical industry.

Theory Outline
The fraction C11-C16 (boiling point 180-280C),

Gives kerosene, mainly used as a fuel in jet engines and diesel engines and as a
fuel (light fuel) for domestic heating.
The fraction exceeding C18 (boiling point > 350C)

Composes atmospheric residue and is used as a fuel (heavy fuel) for industrial
heating (thermal power plants). It is subject to reduced pressure distillation and
produces light (C18-C25, boiling point 300-400C) and heavy lubricating oils (C26-
C36, boiling point 400-500C).
The residues of vacuum distillation are asphalts.
Additional processing exist to upgrade the crude and to produce the largest possible
number of high-value molecules, but the principle is the same and consists of using the
difference between the characteristics of the molecules to obtain the desired product.
5.2. GAS PROCESSING
In sufficient quantities, gas is upgraded by specific gas treatment facilities and is either
commercialised in its gaseous form or as a liquid (after liquefaction) depending on the
distances between the production point and the consumption point.
Frigg Hassi
Lacq Urengo Groningue
(North R'Mel
(France) (Russia) (Netherlands)
Sea) (Algeria)
Methane (%) 95.7 69.2 98 83.5 81.3
Ethane (%) 3.6 3.3-3.6 7.9 2.9
Propane (%) 0.04 1.0-1.2 2.1 0.4
Butane (%) 0.01 0.6-0.9 1.0 0.2
Nitrogen gas (%) 0.4 0.6 1.2 5.3 14.3
Carbon dioxide (%) 0.3 9.3 0.3 0.2 0.9
Hydrogen sulphide (%) - 15.3 - - -
The compositions are given as a volume %.
Figure 24: Characteristics of a number of natural gas deposits

Theory Outline
5.2.1. Transport in gaseous form
In addition to hydrocarbons (which can be upgraded), natural gas contains impurities

which have to be removed in order to prevent problems in the facilities, particularly since
the specifications imposed by the purchasers include identical clauses to preserve their
own facilities.
As far as transport in gaseous form is concerned, it is important to ensure that there is no

formation of liquid in the pipe (condensates and / or water) and no risk of corrosion (CO2 s
and / or H2S)
The pressure and temperature conditions which develop in the pipe may give rise to the
formation of liquids, water or HC.
The formation of liquid must be avoided for three main reasons:
Accumulation of liquids at the low points of the pipe creating liquid slugs and
instabilities in the flow (two phase),
Internal pipe corrosion phenomena if the gas contains H2S or CO2 and water,
Formation of hydrates (water which reacts with HC under particular T/P

conditions).
Over short distances (<30Km) the gas may be transported without treatment ensuring that
there is no hydrate formation and no corrosion phenomena by injecting chemicals (for
example glycol) and by providing liquid recuperation facilities at the discharge point.
For longer distances, it is necessary to dry the gas to a level of dryness that prevents the
formation of hydrates (solid plugs which form by a reaction between the hydrocarbons and
the water they contain, under specific conditions. These plugs may block the pipes).
5.2.2. Transport in liquid form
The liquefaction of gas is a necessary stage in its marketing if transport via a pipeline is
impossible. In this case, it has to be transported by boat and therefore in small
transport-unit volumes and liquefaction which reduces the volume 600 times is therefore
the only possibility for this type of transport.
The treatment of gas before marketing may be more or less complex, depending on the
intended aim and in particular depending on the products required from liquefaction: (LNG,
LPG, Propane, Butane, etc. see Liquefaction).

Theory Outline
Figure 25: Gas processing
A number of processes exist for the liquefaction of natural gas and the chosen process
depends above all on the composition of the gas to be liquefied. This composition will
define the temperature which needs to be attained for liquefaction.
In all cases, the gas is purified by the elimination of undesirable components, particularly
CO2, H2S and H2O, before liquefaction.
The principle of the liquefaction of natural gas is based on a series of "refrigerating cycles",
using one or more cooling gases, alternating compressions, high-pressure condensation
and low-pressure evaporation and expansion.
The succession of these cycles using heat exchangers brings the gas to a sufficiently low
temperature to transform it to its liquid state at atmospheric pressure.
On average a liquefaction plant consumes 12 % of the incoming natural gas for its own
operations.

Theory Outline
The general principle may be represented as follows:
Figure 26: Gas treatment
5.2.2.1. Liquefied natural gas: LNG
Liquefied Natural Gas (LNG): methane (CH4) and ethane (C2H6)
Natural gas consists mainly of methane. Therefore LNG essentially contains methane with
ethane, propane and butane.
GL 4Z KENAI NIKISI MARSA EL BREGA GL 1K
(ALGERIA) (LYBIA) (LYBIA) ALGERIA)
LNG Properties & mole% Actual LNG to ship Actual LNG to ship Actual LNG to ship Actual LNG to ship
N2 (mole %) 0.71 0.40 1.25
C1 86.98 99.60 67.70 92.55
C2 9.35 19.80 5.37
C3 2.33 8.70 0.59
iC4 0.27 0.10
nC4 0.36 3.10 0.14
C5+ 0.60
Molecular weight 18.36 16.39 22.89 17.18
Boiling point at 760mm Hg deg. C -163 -162 -160 -164
Density at storage conditions kg/m3 474 428 537 456
Gas to liquid ratio Sm3/m3 618 636 555 634
Gross calorific value Kcal/Sm3 9920 8879 12 224 9290

Kcal/m3 Liq 6 140 000 5 651 000 6 800 000 5 889 000

Theory Outline
Natural gas is liquefied (at around -163C at atmospheric pressure), transported in this
form by liquid natural gas tankers and restored to is gaseous state on arrival in the user
country.
(-161C=boiling point temperature of methane).
5.2.2.2. LPG liquefied petroleum gas
This is a mixture in variable proportions of propane (C3H8) and Butane (C4H10); propane is
generally the preponderant element.
They are gases under normal temperature and pressure conditions, liquefied and
maintained in their liquid state when the pressure is increased or when the temperature is
reduced.
Liquefied gas is obtained from certain natural gases or from the refining of oil. 60 % of
worldwide production is obtained from natural gas and 40 % from the refining of crude oil
(1 t of oil produces between 20 and 30 kg of LPG in the refining process).
LPG cannot be obtained directly from natural gas (which contains other hydrocarbons:
CH4, C2H6 for example). In order to obtain LPG, it is necessary to go through an
intermediate stage, namely the manufacturing of NGL, which is a mixture of gaseous
hydrocarbons which are liquefied by cooling.
The C3 and C4 mixture is isolated by fractionating NGL in order to obtain LPG.
5.2.2.3. NGL - Natural Gas Liquids
This is a general term which is applied to all liquids obtained from the associated gas.
They are heavier mixtures of ethane and hydrocarbons; propane, butanes, condensates,
etc. They are gaseous in the reservoir (like condensates).
They are liquefied by cryogenics before use and are sold (C3 and C4) under the name of
LPG.
NGL are obtained fairly easily since it is not necessary to cool to very low temperatures.
Boiling point temperature of C2 approximately -88C compared with that of C1 -161C).

Theory Outline
5.2.2.4. Condensates or natural gasoline
(Condensate or natural gasoline): liquid mixture C5 to C8.
During extraction, expansion at the wellhead triggers the condensation of hydrocarbons

C5 to C8 (which were gases in the reservoir conditions). The recovered liquids, known as
natural gas condensates correspond to extremely light oil with a very high value (giving
petroleum and naphtha). The remainder (hydrocarbons C1 to C4, CO2, H2S and He) is
gaseous at room temperature and is dispatched through a pipeline to a gas treatment
factors. Two collection networks are therefore required, one for the gas and one for the
condensates.
The market value of the condensates and the LPG is such that certain deposits are
produced only for this purpose, with the poor gas (methane) being gradually reinjected in
the absence of local outlets. Even when most of the poor gas is sold, a proportion is often
reinjected into the deposit to compensate for the pressure drop and eventually to recover a
larger proportion of condensates and LPG.

Theory Outline
6. HYDROCARBONS AS A SOURCE OF ENERGY
6.1. INTRODUCTION
NB: see also course entitled From atoms to hydrocarbons.
Combustion is a chemical reaction which generates heat. During this reaction, a fuel (in
this case a hydrocarbon) reacts with a combustive fuel (mainly oxygen O2).
The combustion of an organic component produces carbon dioxide (CO2) and water (H2O).
The heat energy produced is related to the transformation of the hydrocarbon molecules,
the principle being that the breaking of the C-H bonds produces much more energy than
required to create bonds for the CO2 and H2O molecules produced by combustion.
NB: the heating value of a fuel is the quantity of heat produced by its combustion at a
constant pressure and under normal temperature and pressure conditions (in other words
at 0C and with a pressure of 1013 mbar).
6.2. COMBUSTION OF ALKANES
The combustion of alkanes in the air is a highly exothermal reaction which is widely used
for the production of heat and mechanical energy.
6.2.1. Example: the combustion of methane:
The chemical reaction corresponding to the combustion of methane ( g: the elements are
gaseous) is written as follows:
CH4 (g) + 2O2 (g) (the reagents) CO2(g) + 2H2O(g) (the products)
The balance equation (see course entitled From atoms to hydrocarbons) shows that this
reaction produces more energy than it consumes and is said to be exothermal. The energy
released (3460 kJ. mol-1) by the creation of product bonds is 820 kJ. mol-1 more than the
quantity consumed ( 2640 kJ. mol-1) to break the reagent bonds (therefore the methane
molecules).
Comments:
The combustion heat of methane is - 820 kJ. mol-1 if water is obtained in the gaseous
state, but is - 890 kJ. mol-1 if water is obtained in the liquid state: the reaction is more
exothermal if the water is in the liquid state (the energy required for the vaporisation of the
water is not expended).

Theory Outline
This explains why the combustion of hydrocarbons produces energy.
Figure 27: Combustion of hydrocarbons
If we express this energy in kJ.kg-1, we simply need to remember that the mass (quantity
of matter) of one mole of an element is equal to the value of its molar mass expressed in
grams. Therefore the molar mass of methane =16g/mol
i.e. 1kg of methane=1000/16 moles, releasing 890 x 1000/16 = 55625 (kJ.kg-1).
In general, the combustion heat of alkanes with N carbon atoms is approximately 658 N+
243 kJ/mole. The first terms are relatively richer in hydrogen and their combustion heat is
slightly more intense.
If we apply this estimation to methane the energy produced = 658+243=901 kJ. mol-1.
The important thing to remember is that the heat energy released by one mole of alkane is
greater when more carbon atoms are present (one mole of a methane molecule is made
up of 6.023 1023 molecules of methane).
By comparison, the combustion of butane (C4H10) produces 11062-8388=2674 kJ/mol

(using the same approach with the corresponding combustion chemical reaction).

Theory Outline
7. NAMES ASSOCIATED WITH HYDROCARBONS
7.1. GAS AND CRUDE
Natural gas and crude oil are often associated and extracted at the same time from the
same deposits or the same production zones.
An average proportion of liquid hydrocarbons, corresponding to around 80%, are obtained

from crude oil; the remaining 20%, among the lightest fractions, contain propane and
butane and are nearly always liquefied to facilitate transport.
7.2. NATURAL GAS
This is a mixture of hydrocarbons which are in a gaseous state under reservoir conditions.
This gas has a high methane content (between 70% and 100%) and consists manly of
gaseous hydrocarbon compounds (C1 to C5). It also contains a smaller quantity of heavier
molecules in gaseous form (nitrogen, carbon dioxide, hydrogen sulphide.)
The production of this gas generally generates liquid hydrocarbons. This liquefaction
occurs during expansion in the production facilities. This is why a natural gas is often
characterised by the associated quantity of condensates.
7.3. CRUDE OIL
Crude oil is a mixture, in variable proportions, of hydrocarbons which are liquid in their
natural state under varying pressure and temperature conditions in their reservoir. It may
contain small quantities of matter other than hydrocarbons.
Crude oils are classified according to their specific gravity or density API as:
extra-heavy: in excess of 1 000 kg/m3 (less than 10 API),
heavy: 1 000-920 kg/m3 (10-22.3 API),
average: 920-870 kg/m3 (22.3-31.1 API).

Theory Outline
7.4. DENSITY OF OIL: THE API DEGREE
Crude oil is classified as light, average and heavy depending on its gravity or density, as
measured on the scale of the American Petroleum Institute (API).
The API degree is used in the Anglo Saxon system to measure the density of an oil,
whereby the temperature is always specified.
API degree (temp)= (141.5/ Density at temp) 131.5.
Density ( temp) = 141.5/( 131.5 + API at temp)
The API density is expressed in API degrees
Examples:
a liquid with a density of 1.00 at 15C (H2O =1kg/litre) has an API density of
10API at15C. (API degree= 141.5/1 131.5 = 10API)
a liquid with 22API at 15C has a density at 15C = 0.9218

(Density at 15C = 141.5/(131.5+22) = 141.5/153.5 = 0.9218)
a liquid with 35API at 15C has a density at 15C = 0.8498

(Density at 15C = 141.5/(131.5+35) = 141.5/166.5 = 0.8498)
The conventional lower limit for oil is generally set at 15API.
Light crude has an API density in excess of 31.1; average crude has a density of between
22.3 and 31.1 and heavy oil has a density of less than 22.3.
7.5. ASSOCIATED GAS
During the production of crude oil, the products extracted from the reservoir are stabilised
at the surface (to evacuate the gases dissolved in the liquid). The gas which is released as
a result is known as the associated gas. The potential of a crude to produce associated
has is known by definition as GOR (gas oil ratio).
GOR = total gas produced (SCF or m3)/ oil produced (bbl or m3).
7.6. ARABIAN LIGHT
Quality of crude oil produced in Saudi Arabia with a density of 34 API.
Its price on leaving the Gulf has formed the reference for OPEC prices for many years.
Theory Outline
7.7. BRENT
Mixture of crude oils produced by seven neighbouring fields in the North Sea linked to the
same pipeline.
7.8. LIGHT AND HEAVY OILS (HYDROCARBONS)
Light oils are hydrocarbons which consist mainly of light molecules (which contain few
carbon atoms) and are therefore essentially:
Methane(CH4)
Ethane(C2H6)
Propane(C3H8)
Butane (C4H10)
Which are all below C5 (see API degree for further details)
7.9. TOE: TONNE OIL EQUIVALENT
This approximate equivalence is used to express combustible reserves of TOE.
1 tonne of oil = 1000 m3 of gas = 1.5 tonnes of coal
7.10. GOR (Gas Oil Ratio)
This is the total volume of gas expressed under standard conditions associated with the
production of a unit volume expressed under reference conditions for storage oil.
It is expressed as m3/m3 standards.
7.11. BSW (Bottom Sediment and Water also known as watercut)
This is the percentage of water and sediments in relation to the liquid phase (oil +water +
sediment).
During a delivery of crude, disregarding sediments, this corresponds to the percentage of

water contained in this crude. BSW = WATER / OIL + WATER.

Theory Outline
7.12. HYDRATES
Hydrates are akin to ice in which a molecule of gas is encaged by molecules of water.
These cages group together and quickly form solid plugs. The hydrates form at fairly high
pressures and low temperatures but free water must always be present to enable the
hydrates to form.
Hydrates may create solid plugs in pipes, preventing the circulation of gas, which is why
before gas is transported though a pipe it is dehydrated to ensure that in the worst case
any water which may remain dissolved in the gas is not transformed into free water.
The precautions to be taken (level of dehydration, P, T) can be obtained by calculations or

from curves.
Hydrates also exist in nature and form pockets of gas in the form of ice which compose a
wonderful source of energy, equivalent to twice the methane from identified reserves of
coal, oil and gas combined.
7.13. DEW POINT
(for H2O and HC).
All gases are products formed from a group of components, particularly different types of
hydrocarbons and water (in gaseous form).
The dew point (for a given pressure) is the temperature above which the component
passes from the gaseous state to the liquid state.
Therefore for water the dew point of a given gas at a given pressure is the temperature
above which water in gaseous form liquefies. The same applies to gaseous hydrocarbons
(HC dew point).
7.14. WATER CONTENT
All gases contain water in their gaseous form. The water content is the quantity of
water/value of gas generally expressed in Kg/Sm3. This value depends on the pressure of
the gas concerned and its temperature.
The water content which is obtained from curves can be used to determine the quantity of
water which must be removed from the gas by the drying process.

Theory Outline
It should be noted that:
For a given gas pressure, the lower the temperature of the gas, the lower the
water content
For a given temperature, the higher the gas pressure, the higher the water
content.
7.15. WOBBE INDEX
This is the highest heating value of a gas divided by the square root of its density; it is a
parameter used to compare the combustion energy of a gas.
Two gases with the same index are interchangeable (from the point of view of the energy
supplied) without altering the combustion system.
It is expressed, for example, in J/m3 .

Theory Outline
8. EXERCISES
1. The 3 molecules below have the same empirical formula C6H14, which ones have
the same carbon chain?
2. Determine the number of constitutional isomers of hexane C6H14

Theory Outline

Theory Outline
3. Name the following molecule:

Theory Outline
9. GLOSSARY

Theory Outline
10. LIST OF FIGURES

Figure 1: Propane ................................................................................................................5
Figure 2: Glycol....................................................................................................................5
Figure 3: Ethylamine ............................................................................................................5
Figure 4: Methane CH4 ........................................................................................................9
Figure 5: Ethane C2H6 .........................................................................................................9
Figure 6: Stereoisomers.....................................................................................................13
Figure 7: Iso-alkanes .........................................................................................................14
Figure 8: Methane CH4 (gas) ..........................................................................................16
Figure 9: Ethane C2H6 (gas) ...........................................................................................16
Figure 10: Propane C3H8 (gas) .......................................................................................16
Figure 11: Butane C4H10 (gas) ........................................................................................16
Figure 12: Pentane C5H12 (liquid) ...................................................................................16
Figure 13: n-butane C4H10 ..............................................................................................17
Figure 14: 2-methyl-propane(isobutane) C4H10 ...............................................................17
Figure 15: Alkane: Ethane C2H6......................................................................................18
Figure 16: Alkene: Ethene C2H4......................................................................................18
Figure 17: Alkenes .............................................................................................................19
Figure 18: The alkynes ......................................................................................................20
Figure 19: Cyclanes ...........................................................................................................21
Figure 20:Phenyl Radical C6H5 ..........................................................................................22
Figure 21:Benzene C6H6 ....................................................................................................22
Figure 22: Composition of a crude oil and raw natural gas ...............................................23
Figure 23: The distillation cuts ...........................................................................................26
Figure 24: Characteristics of a number of natural gas deposits .........................................28
Figure 25: Gas processing.................................................................................................30
Figure 26: Gas treatment ...................................................................................................31
Figure 27: Combustion of hydrocarbons ............................................................................35

Theory Outline
11. LIST OF TABLES

Table 1: The most important hydrocarbons .........................................................................6
Table 2: Number of alkane isomers ...................................................................................12
Table 3: The first 5 alkyl radicals .......................................................................................13
Table 4: The linear alkanes................................................................................................15
Table 5: Linear saturated hydrocarbons or Alkanes ..........................................................16
Table 6: Properties of alkanes ...........................................................................................24

Theory Outline
12. EXERCISE SOLUTIONS

1. The 3 molecules below have the same empirical formula C6H14, which ones have
the same carbon chain?
There is no difference between molecules A and B; they both contain a (linear)

chain of 5 carbon atoms with a CH3 branch on the 2nd carbon atom.
However, molecule C only contains one (linear) chain of 4 carbon atoms and 2 CH3
branches, therefore C is different from A and B.
2. Determine the number of constitutional isomers of hexane C6H14
There are 5 constitutional isomers: the simple chain which defines the normal
isomer:
There are 2 isomers with a single carbon branch:
and there are 2 isomers with 2 carbon branches:

Theory Outline
This molecule is derived from pentane as its longest chain contains 5 carbon atoms
there are 3 identical alkyl radicals (CH3 methyl)- 2 of these radicals are in
position 2 and one radical is on the 4th carbon.
This molecule is therefore 2,2,4-trimethylpentane. but since it contains 8 carbon
atoms and its formula is C8H18 it is isooctane.
This molecule is derived from heptane as its longest chain contains 7 carbon
atoms.- there are 2 alkyl radicals, one CH3 (methyl) on the carbon 2 and one CH2-
CH3 (ethyl) on the carbon 4 This molecule is therefore 4-ethyl-2-methylheptane.
but since it contains 10 carbon atoms and its formula is C10H22 it is isodecane.
This molecule is derived from hexane as its longest carbon chain contains six
carbon atoms. It also contains a double carbon bond C=C, this molecule therefore
belongs to the hexene family. It possesses 2 alkyl radicals(CH3 methyl) which are
bonded to the carbons in positions 3 and 5 this molecule is dimethyl-2-hexene. It
contains 8 carbon atoms and its formula is C8H16. It is not the octane isomer as the
empirical formula of octane is C8H18.


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THEORY OUTLINE

7.2. NATURAL GAS .......................................................................................................36

Training course: EXP-PR-RT030-EN

Explain the origin of hydrocarbons

Interpret the basic chemical principles of Carbon - Hydrogen bonds

Distinguish hydrocarbon components by their names and formulas

Define the composition of isomers

Name the different hydrocarbon groups

Write the chemical formulas of the components in the groups above

Define the main physical characteristics of hydrocarbons

Interpret changes of state in hydrocarbons

Integrate Pressure and Temperature values to define the characteristics of

Name the different stages in the processing of crude oil

Name the different states in the processing of a natural gas

Interpret the combustion of a liquid and / or gas hydrocarbon

Distinguish the different names of crude oils and gases

Training course: EXP-PR-RT030-EN

2. INTRODUCTION TO THE ORGANIC CHEMISTRY OF

Figure 1: Propane Figure 2: Glycol Figure 3: Ethylamine

Alkenes or olefins (former name),

cyclanes or cyclo-alkanes ou les naphtenes

Name of the function/ group Structure of the group Comments

Consisting only of atoms

Contains at least one

Presence of a triple bond

cyclopropane cyvlobutane cyclohexane, etc

Table 1: The most important hydrocarbons

Training course: EXP-PR-RT030-EN

It is this characteristic which makes it possible to manufacture finished (marketable)

Training course: EXP-PR-RT030-EN

2.2. ORIGIN OF HYDROCARBONS

It is therefore necessary to separate these different products (distillation), transform them

Training course: EXP-PR-RT030-EN

2.3. CARBON AND HYDROGEN

Carbon and hydrogen are the 2 components of hydrocarbons.

Hydrogen possesses 1 electron (see periodic table), therefore only layer K is

representation by an empirical formula: CH4 (methane), C2H6 (ethane)

semi-developed formula CH4 and CH3-CH3

Figure 4: Methane CH4 Figure 5: Ethane C2H6

Whilst it is not possible to use a single formula to define hydrocarbons, we can

Training course: EXP-PR-RT030-EN

hydrocarbons together in six different families whose components possess similar

Alkanes (saturated aliphatic carbonaceous chains)

Alkenes (unsaturated aliphatic carbonaceous chains)

Alkynes (unsaturated carbonaceous chains comprising a triple carbon/carbon

Cyclanes (saturated alicyclic carbonaceous chains )

Aromatics (unsaturated cyclic carbonaceous chains comprising a hexagonal

Cyclens (unsaturated cyclic carbonaceous chains )

A molecule is said to be saturated when each carbon atom which composes it

A molecule (saturated or otherwise) is said to be aliphatic when its carbon chain is

A molecule is said to be aromatic when it possesses an unsaturated cycle of 6

Training course: EXP-PR-RT030-EN

We have seen that it is useful to group hydrocarbons together in families in order to

Alkanes are saturated aliphatic carbonaceous chains).

The number of isomers increases rapidly in excess of six carbon atoms.

There are 2 types of isomer:

Isomers which can be differentiated by their spatial geometry are known as

Training course: EXP-PR-RT030-EN

No of C. atoms No of isomers No of C. atoms No of isomers

Table 2: Number of alkane isomers

2.4.2. Constitutional isomers

In order to determine the name of a branched alkane, we consider that it consists of a

When we consider a molecule to be fully developed in space, new cases of isometry in