45
3
3.2.1 Hydrogenation to Fatty
Alcohols
Depending on their chain length, fatty alcohols
have quite different properties:
5 Short-chain C 8 –C 12 alcohols are clear,
high-boiling and oily liquids with a characteristic inherent odor. From C 10 , fatty
alcohols are hardly miscible with water.
5 Starting from myristyl alcohol with a chain
length of C 14 , fatty alcohols have a “wax-like”
consistency.
5 From C 16 on, fatty alcohols aresolid
wax alcohols, which are sold as flakes
or pellets.
BOX: The Oleochemical Industry: Yesterday - Today - Tomorrow
Until the 1990s, large companies
from Europe, the USA and
Japan (e.g. Henkel, Procter and
Gamble, Unilever, Akzo Nobel
or Kao) dominated industrial
oleochemistry. This has changed
significantly in recent decades.
There are several reasons for this
development:
5 The production of basic
oleochemicals must
nowadays be carried out
in continuously operated
large-scale plants in
order to be economical.
However, a complete
fatty acid plant with a
capacity of 100,000 t a −1
(splitting including fatty
acid fractionation and
glycerol processing)
requires an investment of
80–100 million US dollars.
However, a company only
makes this investment if it
can open up new markets
with its products - if possible
locally.
5 Due to strong competition
from Asian companies
and the associated
overcapacities, the
profitability of basic
oleochemicals has
decreased significantly.
5 Since many important
oil plants (7 Chap. 2) are
cultivated in Asia (Malaysia,
Thailand, Indonesia, etc.),
also oleochemical raw
materials are cheaply
available there.
Due to the high cost of capital
and relatively low profit, many
traditional oleochemical
companies have left the market
and left it to Asian companies.
Henkel, for example, first spun
off its oleochemicals activities
under the name Cognis; parts
of Cognis were subsequently
acquired by BASF. Instead,
Henkel specializes more in sales
goods (adhesives, detergents,
cosmetics) that are less
capital-intensive and generate
higher profits. In the long term,
it cannot be ruled out that
the majority of oleochemical
production plants in Europe
and the USA will be taken over
by Asian companies. European
oleochemical companies
wishing to assert themselves
in the market are well advised
to concentrate on specialty
products and open up new
innovative markets.
3.1 · Production of Basic Oleochemicals
3.2 Reactions at the Carboxy Group
of Fatty Acids
At the carboxy group of fatty acids or the ester
group of fatty acid esters, respectively, the same
organic chemistry can be carried out as with
short-chain carboxylic acids. These include, for
example, amination to fatty acid amides or fatty
nitriles and conversion to fatty acid chlorides or
fatty acid anhydrides. Of particular importance,
however, is the reduction of fatty acids and esters
to fatty alcohols already mentioned in the last
section. These, in turn, have a very extensive
follow-up chemistry, in particular to detergents,
and are therefore described in detail in the following 7 Sect. 3.2.1.
3
3.2.1 Hydrogenation to Fatty
Alcohols
Depending on their chain length, fatty alcohols
have quite different properties:
5 Short-chain C 8 –C 12 alcohols are clear,
high-boiling and oily liquids with a characteristic inherent odor. From C 10 , fatty
alcohols are hardly miscible with water.
5 Starting from myristyl alcohol with a chain
length of C 14 , fatty alcohols have a “wax-like”
consistency.
5 From C 16 on, fatty alcohols aresolid
wax alcohols, which are sold as flakes
or pellets.
BOX: The Oleochemical Industry: Yesterday - Today - Tomorrow
Until the 1990s, large companies
from Europe, the USA and
Japan (e.g. Henkel, Procter and
Gamble, Unilever, Akzo Nobel
or Kao) dominated industrial
oleochemistry. This has changed
significantly in recent decades.
There are several reasons for this
development:
5 The production of basic
oleochemicals must
nowadays be carried out
in continuously operated
large-scale plants in
order to be economical.
However, a complete
fatty acid plant with a
capacity of 100,000 t a −1
(splitting including fatty
acid fractionation and
glycerol processing)
requires an investment of
80–100 million US dollars.
However, a company only
makes this investment if it
can open up new markets
with its products - if possible
locally.
5 Due to strong competition
from Asian companies
and the associated
overcapacities, the
profitability of basic
oleochemicals has
decreased significantly.
5 Since many important
oil plants (7 Chap. 2) are
cultivated in Asia (Malaysia,
Thailand, Indonesia, etc.),
also oleochemical raw
materials are cheaply
available there.
Due to the high cost of capital
and relatively low profit, many
traditional oleochemical
companies have left the market
and left it to Asian companies.
Henkel, for example, first spun
off its oleochemicals activities
under the name Cognis; parts
of Cognis were subsequently
acquired by BASF. Instead,
Henkel specializes more in sales
goods (adhesives, detergents,
cosmetics) that are less
capital-intensive and generate
higher profits. In the long term,
it cannot be ruled out that
the majority of oleochemical
production plants in Europe
and the USA will be taken over
by Asian companies. European
oleochemical companies
wishing to assert themselves
in the market are well advised
to concentrate on specialty
products and open up new
innovative markets.
3.1 · Production of Basic Oleochemicals
3.2 Reactions at the Carboxy Group
of Fatty Acids
At the carboxy group of fatty acids or the ester
group of fatty acid esters, respectively, the same
organic chemistry can be carried out as with
short-chain carboxylic acids. These include, for
example, amination to fatty acid amides or fatty
nitriles and conversion to fatty acid chlorides or
fatty acid anhydrides. Of particular importance,
however, is the reduction of fatty acids and esters
to fatty alcohols already mentioned in the last
section. These, in turn, have a very extensive
follow-up chemistry, in particular to detergents,
and are therefore described in detail in the following 7 Sect. 3.2.1.