75
4
shows the principle using the example of methyl
oleate and some unsaturated reaction partners
which have already been successfully used in this
cross-metathesis: methyl acrylate, acrylonitrile
and allyl chloride. This combination of oleochemical and petrochemical starting materials
produces valuable bifunctional compounds.
Metathesis of oleochemicals has now also
found industrial application. The American company Elevance Renewable Sciences, based in
Woodridge (Illinois/USA), has done pioneering
with corresponding unsaturated fatty alcohols and
thus contains two C=C double bonds per ester
molecule, which can react with ethene. By double
ethenolysis with high ethene pressure, two molecules 1-decene split off and a α,ω-unsaturated
ester remains, which in turn can undergo numerous subsequent reactions (. Fig. 4.18).
As already briefly mentioned, asymmetric
alkenes can also be used in cross-metathesis with
oleochemicals, which, however, is usually associated with a large product range. . Figure 4.19
O
O
O
O
O
O
O
O
O
O
O
O
+/- H 2 C CH 2
3
+ 3
+ 3 H 2
O
O
O
O
O
O
. Fig. 4.17 Ethenolysis of triolein
4.2 · Reactions at the C = C Double Bond of Unsaturated Oleochemicals