Ethenolysis

The Ethenolysis is a chemical process for displaying terminal olefins . Chemically, it is a cross metathesis . The general reaction equation in abstract form is:

{\ displaystyle \ mathrm {A {\ mathord {=}} B \ + CH_ {2} {\ mathord {=}} CH_ {2} \ longrightarrow A {\ mathord {=}} CH_ {2} \ + B { \ mathord {=}} CH_ {2}}}

application

In the SHOP process , ethenolysis is used on an industrial scale. For this purpose, the α-olefin mixtures produced in the SHOP process are separated by distillation, the higher molecular weight fraction is isomerized in the liquid phase by alkaline aluminum oxide catalysts and the internal olefins formed are converted back into α-olefins with excess ethene by ethenolysis. Because of the large excess of ethene, the equilibrium of the reaction is shifted to the side of the terminal α-olefins. Rhenium (VII) oxide on aluminum oxide is used as the metathesis catalyst .

Furthermore, methyl oleate , which is obtained from natural oils, can be converted into 1-decene and methyl 9-decenoate by ethenolysis . Another application is the breakdown of natural rubber into low molecular weight polyisoprenes using Grubbs catalysts .

Individual evidence

^ Klaus Weissermel , Hans-Jürgen Arpe : Industrial Organic Chemistry: Important Raw Materials and Intermediates. Wiley-VCH Verlag 2003, ISBN 3-527-30578-5 .
↑ Smaranda C. Marinescu, Richard R. Schrock, Peter Müller, Amir H. Hoveyda: Ethenolysis Reactions Catalyzed by Imido Alkylidene Monoaryloxide Monopyrrolide (MAP) Complexes of Molybdenum . In: J. Am. Chem. Soc. . 131, No. 31, 2009, pp. 10840-10841. doi : 10.1021 / ja904786y .
↑ Yann Schrodi, Thay Ung, Angel Vargas, Garik Mkrtumyan, Choon Woo Lee, Timothy M. Champagne, Richard L. Pederson, Soon Hyeok Hong: Ruthenium Olefin Metathesis Catalysts for the Ethenolysis of Renewable Feedstocks . In: Clean . 36, No. 8, 2008, pp. 669-673. doi : 10.1002 / clen.200800088 .
^ Stefanie Wolf, Herbert Plenio: On the ethenolysis of natural rubber and squalene . In: Green Chem . 13, 2011, pp. 2008–2012. doi : 10.1039 / c1gc15265c .

[1] Klaus Weissermel , Hans-Jürgen Arpe : Industrial Organic Chemistry: Important Raw Materials and Intermediates. Wiley-VCH Verlag 2003, ISBN 3-527-30578-5 .

[2] Smaranda C. Marinescu, Richard R. Schrock, Peter Müller, Amir H. Hoveyda: Ethenolysis Reactions Catalyzed by Imido Alkylidene Monoaryloxide Monopyrrolide (MAP) Complexes of Molybdenum . In: J. Am. Chem. Soc. . 131, No. 31, 2009, pp. 10840-10841. doi : 10.1021 / ja904786y .

[3] Yann Schrodi, Thay Ung, Angel Vargas, Garik Mkrtumyan, Choon Woo Lee, Timothy M. Champagne, Richard L. Pederson, Soon Hyeok Hong: Ruthenium Olefin Metathesis Catalysts for the Ethenolysis of Renewable Feedstocks . In: Clean . 36, No. 8, 2008, pp. 669-673. doi : 10.1002 / clen.200800088 .

[4] Stefanie Wolf, Herbert Plenio: On the ethenolysis of natural rubber and squalene . In: Green Chem . 13, 2011, pp. 2008–2012. doi : 10.1039 / c1gc15265c .