Long-chain α-ω Diols from renewable fatty acids via tandem olefin metathesis-ester hydrogenation

Creator

Angela Gonzalez-De-Castro, Koninklijke DSM N.V.
Elena Cosimi, ETH Zürich
Mae Joanne B. Aguila, University of the Philippines Los Banos
Piotr Gajewski, Faculteit der Natuurwetenschappen
Mike Schmitkamp, Koninklijke DSM N.V.
Johannes G. De Vries, Leibniz Institute for Catalysis
Laurent Lefort, Koninklijke DSM N.V.

Issue Date

3-2017

Abstract

Long chain α-ω diols were readily accessed from renewable fatty acid methyl esters following an orthogonal tandem self-metathesis-ester hydrogenation protocol. By adding a base and a bidentate ligand, the metathesis catalysts were transformed in situ into efficient ester hydrogenation catalysts. The selectivity of the hydrogenation reaction was tuned towards the exclusive formation of either the unsaturated or the saturated diol by modifying the ligand/catalyst ratio. An orthogonal tandem cross-metathesis-ester hydrogenation reaction was also applied for the synthesis of a fragrance compound.

Source or Periodical Title

Green Chemistry

ISSN

1463-9262

Volume

19

Issue

7

Page

1678-1684

Document Type

Article

Language

English

Recommended Citation

Gonzalez-De Castro, A., Cosimi, E., Gajewski, P., Aguila, M.J.B., Schmitkamp, M., de Vries, J.G., Lefort, L., (2017). Long-chain α-ω Diols from renewable fatty acids via tandem olefin metathesis-ester hydrogenation. Green Chemistry, 19 (7), 1678-1684. DOI: 10.1039/C7GC00192D.

Identifier

DOI:10.1039/C7GC00192D

Digital Copy

yes