81
4
temperatures >350 °C. The esters of 10-undecenoic acid can be catalytically copolymerized with
alkenes such as ethene. . Figure 4.26 shows a
obtained from castor oil (7 Sect. 2.2.7), which
can be selectively cleaved into heptanal and
10-undecenoic acid by pyrolysis, i.e. heating to
COOH
OH
Ricinoleic acid
1-Heptanal
Pyrolysis (T > 350 °C)
COOH
10-Undecenoic acid
H 2 N
COOH
H 2 N
COOH
(CH 2 ) 8 C O (CH 2 ) 3
O C
O
O
(CH 2 ) 8
OH
CHO
CHO
1) + HCN
2) + 2 H 2
Nylon 12
Nylon 11 (Rilsan)
1) + HBr
2) + NH 3
Metathesis
+ 1,3Propanediol
[Ru]
CH 2 CH 2
-
Polyesters
Red.
10-Undecenol
Alkoxycarbonylation
[Co]
+ CO
Polyesters
10-Undecenal
Aldol
Condensation
Metathesis
[Ru]
CH 2 CH 2
-
Polymers
Red.
O
O
n
. Fig. 4.26 10-Undecenoic acid and its subsequent chemistry to polymers
4.2 · Reactions at the C = C Double Bond of Unsaturated Oleochemicals