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F32 Fatty acids

Cognis
College
Fatty acids

F32 Fatty acids

Contents
1. Occurrence of the fatty acids

2. Chemical structure

3. Properties of the fatty acids

4. Reference numbers of the fatty acids

5. Extraction of the fatty acids

6. Technical variations and specialties

13

7. Application areas

17

8. Market data

18

9. Trade Names at Cognis

20

10.

Keywords
21

F32 Fatty acids

F32 Fatty acids

Chapter 1
Occurrence of the fatty acids
Fatty acids are a component of the natural oils and fats. They are esterified with
glycerine and form triglycerides.
glycerine part

fatty acid part

o
H2

o
H

o
H2
Fig.. 1

Structure of the fatty acids

C-chain distribution and quantity

The percentage of fatty acids in the oils and fats is different from resource to
resource. Coconuts or palm kernels deliver mainly C12 / C14, tallow or palm oil
mainly C16 / C18, for example.
The most important fatty acids in oleochemicals are found in the following natural
oils and fats:
C8 C10 C12 C14 C16 C18 C20 C22
coconut

48

17

10

palm kernel

50

15

18

tallow

30

65

palm oil

42

56

rich

38

50

poor

90

sunflower

93

soya

91

rape

Fig. 2

C-chain distribution in natural oils and fats

F32 Fatty acids

Chapter 2
Chemical structure
Fatty acids belong to the chemical group of the carboxylic acids. The carboxylic
acids are characterized by a carboxylic (or carboxo) group (COOH) that is attached
to a hydrocarbon chain (abbreviated R).
The carboxylic group is responsible for the acidic effect of these substances,
because it is able to set free a hydrogen ion (H +) when solved in water.

carboxylic
acids

carboxylic
group:

O
C

consists
carbonyl
of
group:

O
C

hydroxyl
Fig. 3

Structure of the carboxylic acids

The chemical name "carboxylic acid" is derived from the basic hydrocarbon to which
the addition "acid" is connected to.
The following table shows a carboxylic acid that is very important in oleochemicals:
lauric acid, C12

carbon chain
Fig. 4

acid group

Structure of the lauric acid

From the number of 4 carbon atoms in the hydrocarbon chain on, the carboxylic
acids are called fatty acids.
Fatty acids from natural oils or fats are always even-chained and have got an even
number of carbon atoms. This is due to the elongation process that takes place in
plants.
A difference is made between saturated and unsaturated fatty acids.
Saturated fatty acids contain only single bonds (C-C) in their hydrocarbon chain.

F32 Fatty acids

Unsaturated fatty acids contain at least one double bond in their hydrocarbon chain
(C=C). If more than one double bond exists, they are called multiple (double, triple
etc.) unsaturated fatty acids.
Here are examples of the C18 fatty acids (fatty acids with 18 carbon atoms):
C 18 fatty acid, saturated
stearic acid (octadecanoic acid) C17 H35 COOH

O
C

C 18 fatty acid, single unsaturated

oleic acid (octadecenoic acid) C17 H33 COOH
H
H

C 18 fatty acid, double unsaturated

linoleic acid (octadecadienoic acid)
C17 H31 COOH

O
C

C 18 fatty acid, triple unsaturated

linolenic acid (octadecatrienoic acid)
H
H

C17 H29 COOH

Fig. 5

C 18-fatty acids

Apart from the chemical names there exist so-called trivial names of the fatty acids
as well. These names were introduced most often with the discovery of the fatty
acids.
The dodecanoic acid for example was first found in the fruits of the laurel tree (Latin:
Laurus nobilis) and was thus called lauric acid.
In the oleochemical terminology still the trivial names are most often used.
The most important fatty acids are the following:
Saturated fatty acids
C6

Hexanoic acid

Caproic acid

C8

Octanoic acid

Caprylic acid

C 10

Decanoic acid

Caprinic acid

C 12

Dodecanoic acid

Lauric acid

C 14

Tetradecanoic acid

Myristic acid

C 16

Hexadecanoic acid

Palmitic acid

C 18

Octadecanoic acid

Stearic acid

F32 Fatty acids

C 20
C 22

Eicosanoic acid
Docosanoic acid

Arachidic acid
Behenic acid

C 24

Tetracosanoic acid

Lignoceroic acid

Unsaturated fatty acids (number of double bonds /.)

C 18 / 1

Octadecenic acid

Oleic acid

C 18 / 2

Octadecadienoic acid

Linoleic acid

C 18 / 3

Octadecatrienoic acid

Linolenic acid

C 20 / 1

Eicosenoic acid

Gadoniloic acid

C 20 / 4

Eicosatetraenoic acid

Arachidic acid

C 22 / 1

Docosenoic acid

Erucic acid

C 22 / 5

Docosapentanoic acid

Clupanodonic acid

The ricinoleic acid is in a special position. It is a single unsaturated fatty acid that
attaches a hydroxyl group (OH) to a C-atom.
Castor oil contains 87 % of the ricinoleic acid that has the chemical name 12-OxyOctadecenic acid.
Ricinoleic acid

C17 H32 OH COOH

Fig. 6

Structure of the ricinoleic acid

To this additional hydroxyl group one can add for example ethylene oxide to get an
emulsifier such as Eumulgin RO40.

F32 Fatty acids

Chapter 3
Properties of the fatty acids
Pure fatty acids are colorless substances. Their melting point rises with the
increasing chain length, the unsaturated fatty acids have got a lower melting point
(mp) than the saturated ones. In the oleo chemistry the solidification point (called
Titer with fatty acids) is indicated which is usually a little lower than the melting
point.
fatty acids

length

Titer/C

mp/C

capronic acid
caprylic acid
capric acid
lauric acid
myristic acid
palmitic acid
stearic acid

C6
C8
C10
C12
C14
C16
C18

-3,4
16
31,3
43,5
54,4
62,9
69,6

4
17
31
43
54
63
71

oleic acid
erucic acid
linoleic acid
linolenic acid

C18/1
C22/1
C18/2
C18/3

13,4
34,7
-5,0
-11

16
34
-5
-11

Fig. 7

Solidification points of the fatty acids

Even the boiling points increase with the rising chain length. By the raising of
number of double bonds the boiling point decreases again. Not every acid can be
measured at usual atmospherically pressure (1013 mbar). For some boiling points
(Bp) one has to lower the pressure and get degrees of centigrade in vacuum.
Therefore the figures /mbar are added. Otherwise the acids are cracked before they
can reach the boiling points.
fatty acid

length

Mp/C

Bp/C/mbar

capronic acid
caprylic acid
Capric acid
lauric acid
myristic acid
palmitic acid
stearic acid
oleic acid
erucic acid
linoleic acid
linolenic acid

C6
C8
C10
C12
C14
C16
C18
C18/1
C22/1
C18/2
C18/3

4
17
31
43
54
63
71
16
34
-5
-11

101/1013
239/1013
270/1013
225/133
250/133
272/133
291/133
229/20
225/13
230/21
232/23

Fig. 8

Boiling points of the fatty acids

The viscosity of the fatty acids rises as well with the increasing chain length and falls
with the increasing number of double bonds.
Fatty acids are soluble in organic solvents (e.g. alcohol, gasoline etc.). The solubility
gets worse with the increasing chain length, but a higher temperature can
compensate this. Water and fatty acids are only hardly soluble at room temperature;
the short chain fatty acids have an advantage over the long chain.

F32 Fatty acids

Chapter 4
Reference numbers of the fatty acids
The reference numbers of the fatty acids are part of the quality specification. They
are measured after the instructions of the Deutschen Gesellschaft fr Fettchemie
(DGF) (German Society for Oleo chemistry) and they allow a clear characterization
of the products.
Since no 100 % clean fatty acid from natural oils and fats exists and since many
products contain a mixture of fatty acids depending on the raw material (e.g. coconut
oil fatty acid) it is important to indicate the distribution of the C-chains in percent.
This C-chain spectrum (see Fig. 2) is measured after DGF C-VI 10 with the help of
the gas chromatography or other chromatographically methods (such as HPLC).
entry of
sample

recorder

separator
tube
Fig. 9

detector

Schematic drawing of a gas chromatograph

Apart from the C-chain distribution a couple of other chemical and physical
parameters are measured that serve the purity control of technical fatty acids.
The iodine value indicates the amount of unsaturated components. The higher the
iodine value, the more double bonds. Most often the measuring of the bromide value
is carried out after Kaufmann (DGF C-V 11 d). The acid value (DGF C-V 2) indicates
the amount of free fatty acids, measured in mg KOH, that are necessary to neutralize
1g of the test substance. The saponification value (DGF C-V 3) is a measure for the
free and bound fatty acids in the test substance. It indicates the amount of mg KOH
that are necessary to saponify 1 g of the substance.
SAPONIFICATION VALUE:
SV

-> free fatty acids

-> fatty acids bound to glycerine

Definition: SV indicates how many mg KOH are necessary for the saponification of 1g fat / oil.

ACID VALUE:

-> free fatty acids

AV

Definition: AV indicates how many mg KOH are necessary to neutralize the free fatty acids in 1g
of fat / oil.

ESTER VALUE:

-> inner esters

EV

Definition: EN indicates how many mg KOH are necessary for the saponification of the esters in
1g of fat / oil.

SV - AV = EV
Fig. 10

Overview of titration numbers

The content of unsaponifiable material (e.g. sterines, vitamins, hydrocarbons etc.) is

another indicator for the quality and is about 0,5 to 2 % with technical fatty acids.
As a physical parameter the solidification point (also called Titer) is important. It
indicates the temperature in C at which a liquid fatty acid reaches its maximum
solidification (DGF C-IV 3 c).

F32 Fatty acids

With low melting fatty acids that do not have a solidification point that is easy to
indicate, the cloud point is indicated instead. That means the temperature in C, at
which a cooled and solidifying fatty acid becomes perceptibly cloudy. (DGF D-III 3).
In order to check the quality of the technical fatty acids, also the color measuring is
used, either by the comparison with color glasses after Lovibond 5 1/4 (DGF CIV 4
b) or after Gardner (DGF C-IV 4 c) or by the comparison with color solutions after
Hazen (also called APHA dye value) (DIN 53409). In this way components that cause
a change of color can be indicated.
1.

TINTOMETRY:

Comparison with coloured glasses

LOVIBOND dye value
GARDNER dye value

2.

COLOMETRY:

Comparison with coloured solutions

Hazen dye value
APHA dye value

3.

PHOTOMETRY:

Measuring of the absorption degree

Principle: reflection / absorption in
- UV range
- visible light
- IR range

Fig. 11

Overview of dye values

All these parameters are dealt with in detail in the course K11 ("Physical and
chemical data for Oleochemicals") and the accompanying brochure. Here only one
general note: The clearer the starting material the higher the quality of our products:
Each reaction or subsequent treatment goes hand in hand with a thermo or
mechanical strain.

Chapter 5
Extraction of the fatty acids
Cognis extracts fatty acids from natural oils and fats.
Partly these raw materials have to be pre-cleaned in order to remove carbohydrates,
sterines, proteines, phosphatides and other impurities.
Especially with the treatment of oils and fats for purposes of nutrition the cleaning
(raffination) is carried out thoroughly. In this process also the so-called free fatty
acids (not bound to glycerine) are removed. These fatty acids (raffination fatty acids
or soap stock fatty acids) get into the technical further treatment.
The main part of the fatty acids for the oleo chemistry is extracted by the hydrolytic
fat splitting.
The chemical base for this process is the dissolving of the ester bond by the addition
of water. Glycerine and fatty acids are the result.

F32 Fatty acids

10

triglyceride
H
H

water

glycerine +

O
O

fatty acid

H
R

O
O

O
H

O
O

O
H

C
O

Fig. 12

Hydrolytic fat splitting

In this process water is added continually to the oils and fats at a temperature of up
to 260 C and a pressure up to 60 bars. In the reaction vessels two phases are
found during the splitting process: An aqueous phase that consists of water and
glycerine and a fatty phase that consists of fat and fatty acids. The split fatty acids
and the glycerine water are removed continually.

oils/fats

water

let-down vessel
steam
autoclave

Fig. 13

glycerine
water

split
fatty acid

Process of the hydrolytic fat splitting

By the addition of alkaline catalysts (ZnO, MgO, CaO) the reaction speed can be
risen. Because these alkaline catalysts form soaps during the splitting process that
are solved in the produced split fatty acid, it is necessary to acidify thereafter in
order to replace the soaps.
At the pressure less splitting at a temperature of 100 C acid catalysts (aromatic
sulfonic acids in combination with sulfuric acid) are applied to rise the speed of the
reaction.
Another method to extract fatty acids from natural oils and fats is the saponification
of these raw materials. Potash lye (KOH) is added to the oils and fats and the result
is glycerine and potash salts of the fatty acids (so-called potassium soap).
triglyceride
H

KOH

glycerine

potassium
soap

H
1

R2

O
O

R2

O
H

O
R

Fig. 14

Saponification of the oils and fats with potash lye

11

F32 Fatty acids

Thereafter hydrochloric acid is acidified: Fatty acids and potassium chloride are the
result.
hydrochloric + potassium
acid
soap

potassium
chloride

+ fatty acid

O
H

Cl

Fig. 15

O
O

Cl

Extraction of fatty acids from potassium soaps

This method is only applied with castor oil today, because the OH-group of the
ricinoleic acid would be destroyed during the splitting process with water (hydrolytic
fat splitting).
The raw fatty acids produced this way still contain residues and unsplitted fatty acid
glycerides (mono- and diglycerides). This is why the split fatty acids are distilled for
cleaning purposes. Thus one gets the so-called distillate fatty acid. It is a fatty acid
mix that corresponds in its composition to the fatty acid that is esterified in the
starting raw oil or -fat.
In order to separate the natural fatty acid mixes in the fatty acids (called fractions or
cuts) different methods are applied:

a) Fractionated distillation
The fractionated distillation is based on the different boiling points of the fatty acids.
The differences are 15 - 30 C with successive, even-numbered fatty acids, so an
extraction of single fatty acid chains is possible up to a purity of 99 %.
With a fractionated distillation of a fatty acid mix from coconut oil in the first
distillation column a mix of caprylic- and capric acid results and lauric acid in the
second column. In a further distillation with higher temperatures one gets the higherboiling fatty acids, C 14.
If it is intended to split up a fatty acid mixture with the same chain length but with
different degrees of saturation (e.g. from palm oil: A mixture from stearic acid, oleic
acid and linoleic acid with myristic- and palmitic acid), the unsaturated components
have at first be changed to saturated ones (see chapter 6: Technical variations).
The differences in boiling temperature between the fatty acids with the same chain
length are too little to get clean fractions without this modification. By the
fractionated distillation one gets e.g. from hardened palm oil fatty acid about 2 % of
myristic acid (C 14), 42 % palmitic acid (C 16) and 50 % stearic acid (C 18).
In order to keep the unsaturated parts, Cognis developed the so-called transwetting
method that is explained in the following:

b) Fractionated crystallization
The method of the fractionated crystallization is based on the different melting points
of the fatty acids and on the fact that melted fatty acids form crystals when they cool
down and slowly get solid again.
Significantly different are the melting points between the saturated fatty acids
(palmitic and stearic acid) and the unsaturated ones (oleic acid) in the tallow fatty

F32 Fatty acids

12

acid. The saturated components have a higher melting point and thus crystallize first
when the melted substance cools down. In a certain temperature range two phases
are found: A liquid one (mainly unsaturated fatty acids) and a solid one in form of
crystals (mainly saturated fatty acids).
Pressing in former times carried out the separation of these phases: The two-phasemixture was wrapped in cloth and a pressure was exerted by hydraulic presses. The
liquid components could thus run off through the clothes.
The parts of the two-phase-mixture can be separated easier than by pressing if a
wetting agent solved in water is added to the mix.
A wetting agent is a substance that causes an adherence of water (wetting) at the
surface of a solid material (e.g. of a crystal). The water together with the wetting
agent keeps the liquid fatty acids away from the direct surroundings of the solid fatty
acid crystals.
This process is called rewetting, because the fatty acid crystals are now wetted by
the water and not, as before, by the liquid fatty acids. The result is a mixture of
emulsion (water/liquid fatty acid crystals) and a suspension (water/solid fatty acids)
that can easily be separated by centrifugation (fast spinning). Thereafter only the
water has to be removed. Cognis developed this rewetting procedure. E.g. fatty
alcohol sulfates can be used as wetting agents.
1. Fatty acid crystals (e.g. stearic acid) are finely
distributed in liquid fatty acid (e.g. oleic acid)

stearic acid
oleic acid

2. Addition of water + wetting agent (e.g. fatty

alcohol sulfate). The stearic acid crystals are no
longer wetted by the oleic acid, but by water
(suspension). The liquid oleic acid is distributed
in the water as small droplets (emulsion).

oleic acid
water
stearic acid

3. By centrifugation (quick spinning) the two

phases are separated.
Fig. 16

Transwetting with the fractionated crystallization

Within Cognis Corp. a solvent process is used instead of water with a wetting agent.

Synthetic fatty acids

In petrochemicals fatty acids can also be produced by the oxidation of paraffines

(alkanes).
The fatty acids extracted this way may also have branched chains and can be of an
uneven number.
The synthetic fatty acids form only a small part of the production of even-chained,
even-numbered fatty acids. The paraffine oxidation is only of significance in the
Eastern European countries and in China.

13

F32 Fatty acids

Chapter 6
Technical variations and specialties
The fatty acids extracted in this way are either sold as "distilled fatty acids"
according to the basic oils or fats (e.g. type coconut/palm kernel) or they are sold as
single fatty acids with different degrees of cleanness by the name of "fractionated
fatty acids" (e.g. caproic acid above 99%).
By the name stearine a mix of palmitic acid (C 16) and stearic acid (C 18) is
meant. In former times this solid fatty acid mixture was made mainly from beef tallow.
Nowadays the stearines are also extracted from hardened palm oil-, fish oil- and
rape oil fatty acids.
Oleine is the technical term for the oleic acid (C 18/1). This liquid product is made
from beef tallow, but also from vegetable oils as palm kernel oil, palm oil and linseed
oil (partly hardened).
One example of the technical variations of fatty acids is the transformation of
unsaturated components into saturated ones. This procedure is called fat hardening
or hydrogenation. By the attachment of hydrogen to a double bond, this is
transformed into a single bond.

...

...

...

Fig. 17

...

Fat hardening (hydrogenation)

Depending on the desired degree of saturation, the addition of hydrogen can be

dosed. In this way, fatty acids can either completely or only partly are hardened. By
the hardening (hydrogenation) the C-chain spectrum of fatty acid mixes changes that
make them easier to split up.

distribution of the
c-chains

C16

C18

soya oil fatty acids

28

53

partial
hydrogenation

46

40

complete
hydrogenation

91

--

Fig. 18

C18/1 C18/2 C18/3

C20

--

--

--

Change of the c-chain distribution by fat hardening

Even the properties of the fatty acids change with the hardening. Hardened fatty
acids are of a lighter color, more color stable and less sensitive to oxidation, i.e. they

F32 Fatty acids

14

are easier to store. With the advanced hardening the solidification point (Titer) rises,
whereas the iodine value falls. For margarine, as an example, often-liquid vegetable
oils are used, which then are hardened to the right consistency.
Multiple unsaturated fatty acids can also be modified in another way: by
conjugation. After this technical operation the double bonds that were in a long
distance from each other are now accumulated and only separated by a single bond.
H
H

15

12

O
C

11

Fig. 19

9,12,15 - Octadecatrien acid

13

9,11,13 - Octadecatrien acid

Conjugation of linolenic acid

This shift of the double bonds is achieved with the help of special alkaline catalysts
at temperatures of about 200 to 300 C and an appropriate pressure at the step of
saponification and following deacetylation.
The conjugated fatty acids react faster and get easier linked with each other, that is
why they are used e.g. in the production of polyurethane foams.
Reactions in which only the arrangement of the single atoms is changed, but in
which the number and kind of atoms remain the same are called isomerizations
(Greek: isos: same, meros: part). Aside from the conjugation another type of
isomerization can be carried out with fatty acids. Natural unsaturated fatty acids
have often got a cis-configuration, i.e. two hydrogen atoms at the double bond show
in the same direction.
With the help of catalysts (e.g. selenium) the unsaturated fatty acids are transformed
into the trans-configuration i.e. the two hydrocarbon atoms at the double bond are on
the opposite of each other.
oleic acid
H
H

Cis-configuration

C
H

melting point: 16,3C

H

O
C

C17 H35 COOH

elaidic acid

trans-configuration
Fig. 20

melting point: 44,5C

Cis-trans-isomerization

By this cis-trans-isomerization the fatty acid changes its physical properties. In the
single unsaturated C 18-fatty acid the oleic acid (chemical name: cis-octradecenic
acid) has got a melting point of 16,3 C, whereas the elaidic acid (chemical name:
trans-octadecenic acid) has got a melting point of 44,5 C.

15

F32 Fatty acids

Another type of isomerisation is the production of iso-stearic acids. In this process

oleic acid (C 18/1) is treated with catalysts and high temperatures, which leads to a
branching of the hydrocarbon chain. After this the double bond is transferred into a
single bond with the help of hydrogen.
stearic acid

C17 H35 COOH

H
H

H
C

iso-stearic acid

Fig. 21

Isomerization of stearic acid

The iso-stearic acids are a by-product of the dimerization of oleic acid. Dimer fatty
acids are dicarbonic acids, i.e. fatty acids that have two carboxylic groups (see
chapter 2). They result from the fusion of two single fatty acids and have thus the
double number of carbon atoms. The carbon chain of the dimer fatty acids can have
a branched or a ring-shaped structure.
tall oil fatty acids/oleic acid
Monomer fatty acid

Dimer fatty acid

Trimer fatty acid

Isostearic acid
liquid, saturated,
oxidation stable

liquid, high molecular weight

Applications: lubricants, cosmetics, dimer acid ethoxylates, cooling lubricant

Parameters: pure clay, 260C

Fig. 22

Dimerization of oleic acid

At the dimerisation that is carried out with special catalysts at temperatures between
180 and 300 C, apart from the dimer fatty acids and the iso-stearic acids also
trimer fatty acids result. They have three times as many carbon atoms as the basic
fatty acids and three carboxylic groups.
Other specialities that can be made of fatty acids are the azelaic acid (chem. name:
nonanoylic acid (C 9):

F32 Fatty acids

16

Fig 23

Structure of the azelaic acid

and the pelargonic acid (chem. name: nonanic acid C 9)

Fig. 24

Structure of the pelargonic acid

The production of these ozone acids is carried out by the effect of oxygen (O) on the
double bonds of the oleic acid (C 18/1): The hydrocarbon chain of the oleic acid is
split up and two C 9-fatty acids result.
Also the ricinoleic acid (chem. name: 12-oxy-octadecene acid) offers possibilities for
modification because of its hydroxyl group (OH) at the 12th carbon atom
(see page 6).
E.g. by hardening (transition from the double bond into a single bond by the
attachment of hydrogen) a 12-oxy-octadecene acid becomes a 12-oxy-octadecane
acid, also called 12-oxy-stearic acid or hardened ricinoleic acid.
Another technical variation is the dehydration, i.e. a separation of water.
H

...

...

...

Fig. 25

H
O
H

...

H
Dehydration

In this way, from the 12-oxy-octadecenic acid an octadecadienoic acid is made that
belongs to the conjugated fatty acids.

Chapter 7
Application areas
The distilled fatty acids based on coconut oil, palm kernel oil, palm oil and tallow
fatty acid and the multiple unsaturated fatty acids based on cotton, peanut,

17

F32 Fatty acids

sunflower, soya bean and rape seed oil can - after neutralization with potash lye or
caustic soda - be used for toiletry soaps, soft soaps, defoaming soaps in detergents
and polishing pastes.
By the reaction with lithium-, aluminum- or calcium oxides one gets metal soaps that
are applied as lubricating fats and cold forming agents in the metal and plastics
industry.
By the processing to yield alkyd resin they are used in the varnish and color
industry. They can be refined to yield fatty acid alkanol amides, fatty acid ethoxylates
and partial esters and then they function as emulsifiers or low foaming cleaners.
From fatty acids furthermore fatty amines and amides are produced as PVClubricating agents.
From stearines (mixture of palmitic acid C 16 and stearic acid C 18) e.g. candles,
lubricating grease, vulcanizing catalysts for the rubber industry, cosmetics,
pharmaceuticals, detergent ingredients and deinking agents for the paper industry
are made.
From oleines (technical oleic acid C 18/1) e.g. soft soaps, basic material for the
production of fabric softeners, defoaming agents for the paper- and nutrition
industry, hair dyeing products, auxiliaries for the plastics- and rubber industry,
flotation auxiliaries for the mining industry and textile auxiliaries are made.
With the fractionated fatty acids the application areas can be determined by the
chain length:
C 6 - 10 fatty acids are used as aromatic agents, essences, humectants and
separating agents in the nutrition industry, as skin oils in the cosmetic industry, for
the surface treatment of tin foils and as a lubricating agent in the metal industry.
C 12 fatty acids are used e.g. after further treatment as emulsifiers and starters at
the production of PVC and as surfactants in detergents and cleaners.
C 14 fatty acids are used e.g. after refinement processes as soap for shaving
foams, as a special cleaning agent and as raw material for detergents and cleaners.
C 16 fatty acids can be applied - after esterification - as vitamins in animal feed and
as lubricating agent.
C 18 fatty acids are applied to inhibit the depositing of solid components e.g. in
fertilizers, pesticides, colors and varnishes or also as chlorides in the paper industry.
C 22 fatty acids may also be used in the paper industry, in an amidated form as
PVC-lubricant or in the production of candles.
Erucic acid - C 22/1 fatty acid is e.g. used (like C 22 saturated) after an amidation in
the plastics industry as lubricant in the PVC-production.
The conjugated fatty acids are often used as raw material for the production of
polyurethane foam.
Dimer and trimer fatty acids play an important role in the production of polyamides.
They are applied e.g. in fusion adhesives, sealing materials and printing inks.

F32 Fatty acids

18

In the production of polyamides the azelaic acids are also used. The azelaic and
pelargonic acids can furthermore be processed to yield alkyd resins, softeners and
fragrances.

Chapter 8
Market data
Worldwide the capacity for fatty acid was 5,48 million tons in the year 2000. The
prognoses for the year 2003 are 6,375 million tons. The utilisation was very low at
4,3 mill tons. The effective capacity is the economic usable value.
In 2000 Asia held the top position with 2,713 million tons, followed by Western
Europe with 1,682 million tons and North America with 1,085 million tons.

World Fatty Acid Capacities, 2000/2003,000 mt

2000

2003

7000

Capacity

Capacity

6000

6.375
5.480

5000
WE

1.682

1.732

Asia

2.713

3.481

America

1.085

1.162

World

5.480

6.375

4000
3000
2000
1000
0

effective Capa = 4.3 mill. mt; Demand ca. 3,8 mill. mt

Fig.26

2000

2003

Fatty acid capacities by continents, 2000 / 2003, 000 mt

Prognoses are also made for the application areas of the fatty acids. Nowadays most
of the fatty acids are used in the production of fatty alcohols, amides, esters and
metal soaps (35-40%) and of detergents, soaps and cosmetics (30-40%). On these
markets a growth is expected.
The production of alkyd resins and candles and the application in the color-, rubberand tire industry is regarded as declining, while the need of the textile-, leather- and
paper auxiliary markets stagnate. The application of fatty acids in lubricants is going
to increase.
All in all an annual growth rate of 2 to 3 % is expected.

19

F32 Fatty acids

The worldwide biggest four fatty acid producers are Uniqema, Cognis, Akzo and the
Acidchem. Furthermore there are the Hindustan Lever and the company Oleon at
the fatty acid market.

F32 Fatty acids

20

Chapter 9
Trade Names at Cognis
The product name for Fatty Acid at the European and Asian Market is Edenor. This
product group is divided into following groups:

Distilled Fatty Acids; based on coconut or palm kernel oil are Edenor K,
Edenor KPK types.
Distilled Fatty Acids; based on tallow are Edenor Edenor Ti types.
Polyunsaturated Fatty acids named are Edenor plus abbreviations.
Conjugated Fatty Acids are Edenor UKD types.
Stearines are Edenor ST types or Edenor FHTi types.
Oleins are Edenor TiO5, FTi, LCU, PK1805 and NSb types.
Fractionated Fatty Acids are Edenor types plus the abbreviation of the fraction
and the C-chain distribution in percent, i.e. Edenor C12 98-100.

Cognis Corp. uses other Trade Names for Fatty Acids. Also they produce special
Fatty Acids, which are explained in chapter 6. Their product names are divided into
following groups:

Stearic Acids & Isostearic Acid

Oleic & Polyunsaturated Acids
Coconut Fatty Acids
Tallow Fatty Acids
Fractionated Fatty Acids
Food Grade Fatty Acids

For this product groups they use the Trade Names Emersol and Emery. The Trade
Names for the Dimer, Trimer and Polybasic Acids are Empol, i.e. Empol 1040
Trimer. Azelaic Acids are Emerox types and the Perlagonic acid is the Emery 1202
type.

21

F32 Fatty acids

Chapter 10
Keywords
The keyword list might be helpful for learning. With adding one sentence or
explanation to each word, one will get a good summary of the present topics..

Sources in nature

Ester

Triglyceride

Laurics

Carboxo group

Trivial names of fatty acids

Peculiarity of the ricinoleic acid

Physical and chemical data

Chain distribution

Saponification value

Iodine value

Ester value

Titration

Titer

Unsaponified matter

Color measurements

Fat splitting

Saponification of oils and fats

Fractionated Distillation/Crystallisation

Fat hardening

Conjugated Double bonds

Isomeric structures

Stearine, Oleine, Paraffine

Dehydration