19
2
All carboxylic acids have an IUPAC designation;
however, this is rarely used in oleochemistry.
Trivial names were often introduced many decades ago.
the trivial name palmitic acid. It is obvious that
these are only even-numbered carboxylic acids.
In fact, odd-numbered carboxylic acids such as
pentadecanoic acid are rarely found in nature.
. Table 2.1 Important saturated fatty acids
Abbreviation
IUPAC name
Trivial name
Occurrence
C8:0
Octanoic acid
Caprylic acid
Butter, coconut oil
C10:0
Decanoic acid
Capric acid
Butter, coconut oil
C12:0
Dodecanoic acid
Lauric acid
Animal fats, coconut oil
C14:0
Tetradecanoic acid
Myristic acid
Animal fats, coconut oil
C16:0
Hexadecanoic acid
Palmitic acid
Animal fats, palm oil
C18:0
Octadecanoic acid
Stearic acid
Animal fats, palm oil
C20:0
Eicosanoic acid
Arachidic acid
Peanut, beet and cocoa oil
C22:0
Docosanoic acid
Behenic acid
Canola oil, peanut oil
2.1 · Introduction to Oleochemistry
BOX: The Lazy Oleochemist
The oleochemist often makes it
a little easier and describes the
fatty acids with an abbreviation.
In this abbreviation stands first
the symbol of carbon, followed
by the number of carbon atoms.
Then comes after a colon the
number of C=C double bonds.
Stearic acid is therefore C18:0
acid, palmitic acid C16:0 acid
and oleic acid C18:1 acid
(. Fig. 2.1). If the oleochemist
still wants to indicate at which
position the double bond
is located, he writes this in
brackets after a large Greek
delta Δ. If he wants to indicate
a cis double bond, this is
done with the abbreviation
“c.”, a trans-double bond
correspondingly with “t.”. The
complete abbreviation for
oleic acid is therefore: C18:1
(Δ9/c.). If there are several
double bonds in the fat chain,
these are listed one after the
other in parentheses. The
eicosapentaenoic acid in fish
oil, for example, consists of 20
C-atoms and has five cis double
bonds in positions 5, 8, 11, 14
and 17; the abbreviation is C20:5
(Δ5, 8, 11, 14, 17/all c.).
Which long-chain carboxylic acids are found
in natural fats? Here, somewhat different data are
given in the literature, but usually the even-numbered saturated or unsaturated aliphatic carboxylic acids in the C number range between C8 and
C22 are included; in exceptional cases, also carboxylic acids up to C30 are considered. In very
rare cases, fatty acids with chains that contain an
aliphatic cycle or are branched are also found.
The most important saturated fatty acids are
listed below in . Table 2.1 and the most important unsaturated fatty acids in . Table 2.2. This
information is not intended for memorization,
but for reference.
In addition to these fatty acids, which have
exclusively an aliphatic hydrocarbon rest, there
are also some fatty acids, which carry a further
functional group, e.g. a hydroxy, keto or epoxy
group, in addition to the carboxyl group. The
best-known representatives of these fatty acids
are listed in . Fig. 2.2.
In the following, 7 Sect. 2.2 the plants and
animals are introduced, in which fats with
the most different fatty acid patterns occur.
7 Chapter 3 explains the technical processing of fats into fatty esters, fatty alcohols and
fatty amines. In 7 Chap. 4, you will find an
overview of the further follow-up chemistry
of fats, especially unsaturated oleochemicals. In 7 Chap. 5, we then turn to glycerol,
the inevitable by-product of oleochemistry
(. Fig. 2.1).
2
All carboxylic acids have an IUPAC designation;
however, this is rarely used in oleochemistry.
Trivial names were often introduced many decades ago.
the trivial name palmitic acid. It is obvious that
these are only even-numbered carboxylic acids.
In fact, odd-numbered carboxylic acids such as
pentadecanoic acid are rarely found in nature.
. Table 2.1 Important saturated fatty acids
Abbreviation
IUPAC name
Trivial name
Occurrence
C8:0
Octanoic acid
Caprylic acid
Butter, coconut oil
C10:0
Decanoic acid
Capric acid
Butter, coconut oil
C12:0
Dodecanoic acid
Lauric acid
Animal fats, coconut oil
C14:0
Tetradecanoic acid
Myristic acid
Animal fats, coconut oil
C16:0
Hexadecanoic acid
Palmitic acid
Animal fats, palm oil
C18:0
Octadecanoic acid
Stearic acid
Animal fats, palm oil
C20:0
Eicosanoic acid
Arachidic acid
Peanut, beet and cocoa oil
C22:0
Docosanoic acid
Behenic acid
Canola oil, peanut oil
2.1 · Introduction to Oleochemistry
BOX: The Lazy Oleochemist
The oleochemist often makes it
a little easier and describes the
fatty acids with an abbreviation.
In this abbreviation stands first
the symbol of carbon, followed
by the number of carbon atoms.
Then comes after a colon the
number of C=C double bonds.
Stearic acid is therefore C18:0
acid, palmitic acid C16:0 acid
and oleic acid C18:1 acid
(. Fig. 2.1). If the oleochemist
still wants to indicate at which
position the double bond
is located, he writes this in
brackets after a large Greek
delta Δ. If he wants to indicate
a cis double bond, this is
done with the abbreviation
“c.”, a trans-double bond
correspondingly with “t.”. The
complete abbreviation for
oleic acid is therefore: C18:1
(Δ9/c.). If there are several
double bonds in the fat chain,
these are listed one after the
other in parentheses. The
eicosapentaenoic acid in fish
oil, for example, consists of 20
C-atoms and has five cis double
bonds in positions 5, 8, 11, 14
and 17; the abbreviation is C20:5
(Δ5, 8, 11, 14, 17/all c.).
Which long-chain carboxylic acids are found
in natural fats? Here, somewhat different data are
given in the literature, but usually the even-numbered saturated or unsaturated aliphatic carboxylic acids in the C number range between C8 and
C22 are included; in exceptional cases, also carboxylic acids up to C30 are considered. In very
rare cases, fatty acids with chains that contain an
aliphatic cycle or are branched are also found.
The most important saturated fatty acids are
listed below in . Table 2.1 and the most important unsaturated fatty acids in . Table 2.2. This
information is not intended for memorization,
but for reference.
In addition to these fatty acids, which have
exclusively an aliphatic hydrocarbon rest, there
are also some fatty acids, which carry a further
functional group, e.g. a hydroxy, keto or epoxy
group, in addition to the carboxyl group. The
best-known representatives of these fatty acids
are listed in . Fig. 2.2.
In the following, 7 Sect. 2.2 the plants and
animals are introduced, in which fats with
the most different fatty acid patterns occur.
7 Chapter 3 explains the technical processing of fats into fatty esters, fatty alcohols and
fatty amines. In 7 Chap. 4, you will find an
overview of the further follow-up chemistry
of fats, especially unsaturated oleochemicals. In 7 Chap. 5, we then turn to glycerol,
the inevitable by-product of oleochemistry
(. Fig. 2.1).