Selective Ruthenium‐Catalyzed Hydroaminomethylation of Unsaturated Oleochemicals

Rhodium‐catalyzed hydroaminomethylation (HAM) is recently described as an innovative way to functionalize triglycerides. In the search to reduce production costs, rhodium is sought to be replaced by ruthenium whose price is currently more than 20 times lower. In this study, HAM of unsaturated oleoch...

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Bibliographic Details
Published in:European journal of lipid science and technology 2020-01, Vol.122 (1), p.n/a
Main Authors: Cousin, Kévin, Hapiot, Frédéric, Monflier, Eric
Format: Article
Language:English
Subjects:
Acetonitrile
Amines
Amino groups
Catalysis
Catalytic activity
Chemical Sciences
hydroaminomethylation
Industrial areas
Lubricants
methyl undecenoate
Phosphine
Phosphines
Pollutants
Polymers
Production costs
Rhodium
Ruthenium
Solvents
Surfactants
Triglycerides
triolein
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Summary:Rhodium‐catalyzed hydroaminomethylation (HAM) is recently described as an innovative way to functionalize triglycerides. In the search to reduce production costs, rhodium is sought to be replaced by ruthenium whose price is currently more than 20 times lower. In this study, HAM of unsaturated oleochemicals using ruthenium precursors is proceeded under phosphine‐free conditions. The experimental conditions are optimized by changing the nature of the solvent, the reaction temperature, and the CO/H2 pressure. While rhodium leads to good catalytic activity and low chemoselectivity (mixture of hydroxyl and amino groups), ruthenium proves to be less active but more chemoselective as amino‐substituted products are mainly formed. Of interest, HAM of methyl 10‐undecenoate (MU) occurs in a highly chemo‐ and regioselective fashion using acetonitrile as solvent. Practical Applications: Selective Ru‐catalyzed hydroaminomethylation can be implemented on an industrial scale for the conversion of unsaturated oleochemicals into amines. This finding is of importance as the obtained amino‐products can be used in many industrial areas such as surfactants, polymers, or lubricants. Ru‐catalyzed hydroaminomethylation selectively converts unsaturated oleochemicals into amino‐products under CO/H2 pressure.
ISSN:1438-7697
1438-9312
DOI:10.1002/ejlt.201900131