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Tertiary Amines as Ligands in a Four‐Step Tandem Reaction of Hydroformylation and Hydrogenation: An Alternative Route to Industrial Diol Monomers
Author(s) -
Fuchs Sarah,
Lichte Dominik,
Dittmar Morten,
Meier Gregor,
Strutz Heinz,
Behr Arno,
Vorholt Andreas J.
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201601518
Subject(s) - hydroformylation , catalysis , chemistry , diol , aldehyde , olefin fiber , rhodium , organic chemistry , dicyclopentadiene , tertiary amine , triethylamine , combinatorial chemistry , polymerization , polymer
A highly selective synthesis of diols is presented by simple auto‐tandem catalysis to connect hydroformylation and hydrogenation reactions by a rhodium‐catalyst with tertiary amines as ligands. This system allows the hydroformylation/hydrogenation of non‐conjugated cyclic olefins to selectively provide diols under mild reaction conditions. As a model substrate, the industrially relevant dicyclopentadiene (dcpd) was chosen. With the reaction system [Rh(octanoate) 2 ] 2 and triethylamine, diols are produced in a high yields of up to 79 % with full conversion of intermediate aldehyde and no evidence of olefin hydrogenation. The scope of the reaction was evaluated and the optimised reaction conditions were successfully scaled up to a 2 L reactor. Finally, the Rh/amine catalyst complex was recycled by a simple water extraction of the diol‐product.