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Chapter 4 · There is More to Oleochemistry - Reactions at the Fatty Acid Alkyl Chain
4
cological activity. By tin catalysis, the epoxy
three-membered ring can be extended with carbon dioxide to form the five-membered ring of a
cyclic carbonate.
subsequent reactions of the epoxide group
take place while retaining the three-membered
ring structure, e.g. the conversion with sodium
azide to the aziridines, which possess pharma. Fig. 4.3 Complete
epoxidation of triolein with
performic acid
O
O
O
O
O
O
O
O
O
O
O
O
+ 3 HCOOOH
- 3 HCOOH
O
O
O
C
C
O
+ R''OH
C
C R'
R
OR'' OH
+ Et 2 NH
C
C R'
R
NEt 2 OH
[ZnCl 2 ]
+ HOAc
C
C R'
R
OAc OH
+ CO 2
[Sn]
C
C R'
R
O
O
O
+ NaN 3
C
C
N
H
+ H 2 O
[H + ]
C
C R'
R
OH
OH
Diols
H
H
H
H
H
H
H
H
H
H
H
H
H
H
R'
R
R'
R
. Fig. 4.4 Some subsequent reactions of the fatty epoxides