56
Chapter 3 · The Basics of Oleochemistry - Basic Oleochemicals
3
Production of fatty amines from fatty acids
(or their esters) occurs in two stages (. Fig. 3.23):
5 In the first stage, fatty nitriles are produced by
reaction with ammonia via the intermediate
stage of fatty amides. This releases a total of
two moles of water, which means that dehydrating catalysts are required. In industry,
the reaction with ammonia is carried out in
3.2.3 Conversions to Fatty Amines
As already mentioned at the beginning, nitrogencontaining fats are also of industrial importance.
Fatty amines in particular are coveted intermediates, as they are used for the production of
ammonium compounds with long alkyl chains,
which are used as cationic surfactants.
. Fig. 3.22 Some
follow-up reactions of
Guerbet alcohols
Guerbet alcohols
Guerbet acids
Ox.
- H 2 O
- H 2 O + R´´OH
Guerbet ester
NaOH
SO 3
Guerbet sulfates
+ n EO
Guerbet alcohol ethoxylates
Guerbet alcohol ether sulfates
NaOH
SO 3
OSO 3 Na
R'
R
OH
R'
R
OH
R'
R
O
O
R'
R
O
R''
O
R'
R
O H
n
O
R'
R
O SO 3 Na
n
- H 2 O
COOH
Fatty nitrile
+ NH 3
COO NH 4
- H 2 O
C
O
NH 2
- H 2 O
C N
CH NH
Imine
+ H 2
+ H 2
CH 2 NH 2
Prim. Amine
CH 2 NH 2
R
+
CH NH 2
HN CH 2
+ H 2
- NH 3
CH 2
HN CH 2
Sec. Amine
CH NH
R
+
CH 2
N CH 2
CH
NH 2
+ H 2
- NH 3
N CH 2
Tert. Amine
3
. Fig. 3.23 Production of fatty amines from fatty acids (via fatty nitriles)